Pesticidally active oxime and hydrazone derivatives

ABSTRACT

The present invention relates to compounds of formula (I) as defined herein, to processes for preparing them, to pesticidal, in particular insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control pests such as insect, acarine, mollusc and nematode pests.

RELATED APPLICATION INFORMATION

This application is a 371 of International Application No.PCT/EP2016/062335, filed 01 Jun. 2016, which claims priority to EPpatent application No. 15170862.5, filed 05 Jun. 2015, the contents ofwhich are incorporated herein by reference herein.

The present invention relates to compounds of formula (I), to processesfor preparing them, to pesticidal, in particular insecticidal,acaricidal, molluscicidal and nematicidal compositions comprising themand to methods of using them to combat and control pests such as insect,acarine, mollusc and nematode pests.

Heterocyclic compounds with pesticidal activity are known and described,for example, in WO09/102736, WO11/017505, WO12/109125, WO13/116052,WO13/116053 and WO14/011429. There have now been found novel pesticidalactive oximes and hydrazones.

Accordingly, embodiment 1 is a compound of formula (I),

wherein,

Ar¹ and Ar² are independently selected from phenyl, thienyl, pyridyl,pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, pyrazolyl, thiazolyl,imidazolyl, oxazolyl and isoxazolyl, wherein said phenyl, thienyl,pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furanyl, pyrazolyl,thiazolyl, imidazolyl, oxazolyl and isoxazolyl are unsubstituted orsubstituted by one to three substituents independently selected fromC₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃₋₈cycloalkylC₀₋₆alkyl,C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃₋₈halocycloalkylC₀₋₆alkyl, C₁-C₃haloalkyl-C₃-C₆cycloalkyl,heterocyclylC₀₋₆alkyl, halogen, cyano, cyano-C₁-C₄alkyl,cyano-C₃-C₆cycloalkyl, nitro, C₁-C₆alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkoxy-C₁-C₄alkyl, —S—C₁-C₆alkyl, —S(O)—C₁-C₆alkyl, —S(═O)₂C₁-C₆alkyl, —S(═O)(═NH)C₁-C₆alkyl, —S—C₁-C₆haloalkyl,—S(O)—C₁-C₆haloalkyl, —S(═O)₂ C₁-C₆haloalkyl, —S(═O)(═NH)C₁-C₆haloalkyl,C₁-C₆alkylamino, C₂-C₆dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₆alkylcarbonyl, CHO,C₂-C₆alkoxycarbonyl, C₂-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl,C₁-C₆haloalkylaminocarbonyl or C₁-C₄ dialkylaminocarbonyl;

X¹ is O or NR⁶;

X² is a bond or (CR⁴R⁵)_(n);

n is 1 or 2;

W is O or NR²

Y is oxygen or sulfur;

R¹ and R^(y) are independently hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₃-C₆-cycloalkyl or C₁-C₃-alkoxy; R⁶, R² and R³ are independentlyselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₆-cycloalkylC₀₋₆alkyl, C₃₋₈halocycloalkylC₀₋₆alkyl, C₂-C₆-alkenyl,C₂-C₆haloalkenyl, C₂-C₆-alkynyl, C₂-C₆haloalkynyl,C₁-C₄alkoxy-C₁-C₄alkyl, —S(O)—C₁-C₆alkyl, —S(═O)₂ C₁-C₆alkyl,—S(O)—C₁-C₆haloalkyl, —S(═O)₂ C₁-C₆haloalkyl, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl,C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy,C₃-C₆dialkylaminocarbonyloxy and —C(═N—C₁-C₄alkoxy)-C₁-C₄alkyl; providedthat when R₂ and R₃ are different from hydrogen, R₂ and R₃ isunsubstituted or substituted by one to three substituents independentlyselected from C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl,halogen, cyano, nitro, C₁-C₆alkoxy, C₁-C₆haloalkoxy, —S—C₁-C₆alkyl,—S(O)—C₁-C₆alkyl, —S(═O)₂ C₁-C₆alkyl, —S(═O)(═NH)C₁-C₆alkyl,C₁-C₄alkylamino, C₂-C₆dialkylamino, C₃-C₆cycloalkylamino,C₁-C₄alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl,C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl and C₂-C₈dialkylaminocarbonyl;

R⁴ and R⁵ are independently selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl and C₁-C₆-alkoxy;

J is phenyl or heteroaryl;

or J and R^(y) together with carbon atom to which they are attached forma 9 to 11 membered fused bicyclic ring system; wherein said phenyl,heteroaryl or 9 to 11 membered fused bicyclic ring system isunsubstituted or substituted with one to three substituentsindependently selected from C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl,C₃₋₈cycloalkylC₀₋₆alkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl,C₂-C₆haloalkynyl, C₃₋₈halocycloalkylC₀₋₆alkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, heterocyclylC₀₋₆alkyl, halogen, cyano,cyano-C₁-C₄alkyl, cyano-C₃-C₆cycloalkyl, nitro, C₁-C₆alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkoxy-C₁-C₄alkyl, —S—C₁-C₆alkyl,—S(O)—C₁-C₆alkyl, —S(═O)₂ C₁-C₆alkyl, —S(═O)(═NH)C₁-C₆alkyl,C₁-C₆alkylamino, C₂-C₆dialkylamino, C₃-C₆cycloalkylamino,C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₁-C₆alkylcarbonyl, CHO,C₁-C₆alkoxycarbonyl, C₁-C₆haloalkoxycarbonyl, C₁-C₆alkylaminocarbonyl,C₁-C₆haloalkylaminocarbonyl and C₁-C₄ dialkylaminocarbonyl;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Definitions

The term ‘halogen’ as used herein refers to a fluoro, chloro, bromo oriodo.

As used herein, the term “C₂₋₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond. Theterm “C₁₋₄alkyl” is to be construed accordingly. Examples of C₁₋₆alkylinclude, but are not limited to, methyl, (R)-methyl, ethyl, n-propyl,1-methylethyl (iso-propyl), n-butyl, n-pentyl and 1,1-dimethylethyl(t-butyl).

As used herein, the term “C₂₋₆alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond, having from two to sixcarbon atoms, which is attached to the rest of the molecule by a singlebond. The term “C₂₋₄alkenyl” is to be construed accordingly. Examples ofC₂₋₆alkenyl include, but are not limited to, ethenyl, prop-1-enyl,but-1-enyl, pent-1-enyl, pent-4-enyl and penta-1,4-dienyl.

As used herein, the term “C₂₋₆alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from two to sixcarbon atoms, and which is attached to the rest of the molecule by asingle bond. The term “C2-4alkynyl” is to be construed accordingly.Examples of C2-6alkynyl include, but are not limited to, ethynyl,prop-1-ynyl, but-1-ynyl, pent-1-ynyl, pent-4-ynyl and penta-1,4-diynyl.

As used herein, the term “C₁₋₆haloalkyl” refers to C₁₋₆alkyl radical, asdefined above, substituted with one or more of the same or differenthalogen atoms, as defined above. Examples of halogenC₁₋₆alkyl include,but are not limited to, trifluoromethyl, difluoromethyl, fluoromethyl,trichloromethyl, 2,2,2-trifluoroethyl, 1,3-dibromopropan-2-yl,3-bromo-2-fluoropropyl and 1,4,4-trifluorobutan-2-yl.

As used herein, the term ‘C₂₋₆haloalkenyl’ as used herein refers to aC₂₋₆ alkenyl radical, as defined herein, substituted with one or more ofthe same or different halogen atoms, e.g for example, 2,2-difluorovinylor 1,2-dichloro-2-fluoro-vinyl.

As used herein, the term ‘C₂₋₆haloalkynyl’ as used herein refers to aC₂₋₆ alkynyl radical, as defined herein, substituted with one or more ofthe same or different halogen atoms, for example 1-chlor-prop2-ynyl.

As used herein, the term “C₁₋₆alkoxy” refers to a radical of the formula—OR_(a) where R_(a) is a C₁₋₆alkyl radical as generally defined above.Examples of C₁₋₆alkoxy include, but are not limited to, methoxy, ethoxy,propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, and hexoxy.

As used herein, the term “C₁₋₆haloalkoxy” refers to C₁₋₆alkoxy radical,as defined above, substituted by one or more halo radicals, as definedabove. Examples of halogenC₁₋₆alkoxy include, but are not limited to,trifluoromethoxy, difluoromethoxy, fluoromethoxy, trichloromethoxy,2,2,2-trifluoroethoxy, 1,3-dibromopropan-2-yloxy,3-bromo-2-fluoropropyloxy and 1,4,4-trifluorobutan-2-yloxy.

As used herein, the term “C₁₋₆alkylcarbonyl” refers to a radical of theformula —C(═O)—R_(a) where R_(a) is a C₁₋₆alkyl radical as definedabove.

As used herein, the term “C₁₋₆alkylcarbonylC₁₋₆alkyl” refers to aradical of the formula —R_(a)—C(═O)—R_(a) where each R_(a) isindependently a C₁₋₆alkyl radical as defined above. The carbon atom ofthe carbonyl group may be bonded to any carbon atom in either alkylradical.

As used herein, the term “C₁₋₆alkoxycarbonyl” refers to a radical of theformula —C(═O)—O—R_(a) where R_(a) is a C₁₋₆alkyl radical as definedabove.

As used herein, the term “C₁₋₆alkoxycarbonylC₁₋₆alkyl” refers to aradical of the formula —R_(a)—C(═O)—O—R_(a) where each R_(a) isindependently a C₁₋₆alkyl radical as defined above.

As used herein, the term “C₁₋₆alkylamino” refers to a radical of theformula —NH—R_(a) where R_(a) is a C₁₋₆alkyl radical as defined above.

As used herein, the term “C₁₋₆dialkylamino” refers to a radical of theformula —N(R_(a))—R_(a) where each R_(a) is a C₁₋₆alkyl radical, whichmay be the same or different, as defined above.

As used herein, the term “C₃₋₈cycloalkylC₀₋₆alkyl” refers to a stablenon-aromatic monocyclic hydrocarbon radical consisting solely of carbonand hydrogen atoms, having from three to eight carbon atoms, and whichis saturated or unsaturated and attached to the rest of the molecule bya single bond or by a C₁₋₆alkyl radical as defined above. Examples ofC₃₋₈cycloalkylC₀₋₆alkyl include, but are not limited to, cyclopropyl,cyclopropyl-methyl, cyclobutyl, cyclobutyl-ethyl, cyclopentyl,cyclopentyl-propyl, cyclohexyl, cycloheptyl and cyclooctyl.

As used herein, the term “C₃₋₈halocycloalkylC₀₋₆alkyl” as used hereinrefers to a C₃₋₈cycloalkylC₀₋₆alkyl radical as defined hereinsubstituted with one or more of the same or different halogen atoms.

As used herein, the term “heterocyclyl” or “heterocyclic” refers to astable 5- or 6-membered non-aromatic monocyclic ring radical whichcomprises 1, 2, or 3, heteroatoms individually selected from nitrogen,oxygen and sulfur. The heterocyclyl radical may be bonded via a carbonatom or heteroatom. Examples of heterocyclyl include, but are notlimited to, azetidinyl, oxetanyl, pyrrolinyl, pyrrolidyl,tetrahydrofuryl, tetrahydrothienyl, piperidyl, piperazinyl,tetrahydropyranyl, morpholinyl or perhydroazepinyl.

As used herein, the term “heterocyclylC₀₋₆alkyl” refers to aheterocyclic ring as defined above which is attached to the rest of themolecule by a single bond or by a C₁₋₆alkyl radical as defined above.

As used herein, the term “heteroaryl” refers to a 5- or 6-memberedaromatic monocyclic ring radical which comprises 1, 2, 3 or 4heteroatoms individually selected from nitrogen, oxygen and sulfur. Theheteroaryl radical may be bonded via a carbon atom or heteroatom.Examples of heteroaryl include, but are not limited to, furyl, pyrrolyl,thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl,isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl orpyridyl.

The term “9 to 11 membered fused bicyclic ring system” includes but isnot limited to the following ring systems indolinyl, indanyl, indolyl,isoindolinyl, isoindolyl, indenyl, benzofuranyl, benzothiophenyl,indazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzoxazinyl,benzopyranyl, benzothiopyranyl, quinolinyl, isoquinolinyl, chromenyl,cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,furopyridinyl, naphthyl, dihydrobenzoxazinyl, dihydrochromenyl,dihydrobenzodioxinyl, tetrahydroquinolinyl, tetrahydroquinoxalinyl,tetrahydronaphthalenyl dihydrobenzofuranyl, dihydrobenzopyranyl,dihydrobenzothiopyranyl, dihydrobenzothiophenyl,dihydrodioxinopyridinyl, dihydroindenyl, dihydropyrrolopyridinyl,dihydropyrrolopyrimidinyl, dihydropyrrolopyrazinyl,dihydropyrrolopyridazinyl, pyrrolopyridinyl, pyrrolopyrazinyl,pyrrolopyridazinyl, pyrrolopyrimidinyl, furopyrimidinyl, furopyrazinyl,furopyridazinyl, thienopyridinyl, thienopyrazinyl, thienopyridazinyl,thienopyrimidinyl, pyrazolopyridinyl, pyrazolopyrazinyl,pyrazolopyridazinyl, pyrazolopyrimidinyl, imidazopyridinyl,imidazopyrazinyl, imidazopyridazinyl, imidazopyrimidinyl,thiazolopyridinyl, thiazolopyrazinyl, thiazolopyridazinyl,thiazolopyrimidinyl, oxazolopyridinyl, oxazolopyrazinyl,oxazolopyridazinyl, oxazolopyrimidinyl, pyridopyrazinyl,pyridopyridazinyl, pyridopyrimidinyl, pyridooxazinyl, pyrazinooxazinyl,pyridazinooxazinyl, pyrimidooxazinyl, dihydropyridooxazinyl,dihydropyrazinooxazinyl, dihydropyridazinooxazinyl,dihydropyrimidooxazinyl, dihydropyranopyridinyl, dihydropyranopyrazinyl,dihydropyranopyridazinyl, dihydropyrimidinyl, pyranopyridinyl,pyranopyrimidinyl, pyranopyrazinyl, pyranopyridazinyl,dihydrodioxinopyridinyl, dihydrodioxinopyrazinyl,dihydrodioxinopyridazinyl, dihydrodioxinopyrimidinyl,tetrahydronaphthyridinyl, tetrahydropyridopyridazinyl,tetrahydropyridopyrazinyl, tetrahydropyridopyrimidinyl,tetrahydropyrazinopyridazinyl, tetrahydropteridinyl,tetrahydropyrazinopyrazinyl, tetrahydroquinolinyl, tetrahydrocinnolinyl,tetrahydroquinazolinyl, tetrahydroquinoxalinyl, thiinopyridinyl,thiinopyrazinyl, thiinopyridazinyl, thiinopyrimidinyl,dihydrothiinopyridinyl, dihydrothiinopyrazinyl,dihydrothiinopyridazinyl, dihydrothiinopyrimidinyl,dihydrofuropyridinyl, dihydrofuropyrazinyl, dihydrofuropyridazinyl,dihydrofuropyrimidinyl, dihydrothienopyridinyl, dihydrothienopyrazinyl,dihydrothienopyridazinyl, dihydrothienopyrimidinyl,dihydrocyclopentapyridinyl, dihydrocyclopentapyrazinyl,dihydrocyclopentapyridazinyl, dihydrocyclopentapyrimidinyl,quinolinonyl, naphtyridinonyl, pyridopyrazinonyl, pyridopyridazinonyland pyridopyrimidinonyl.

As used herein, when one embodiment refers to several other embodimentsby using the term “according to any one of”, for example “according toany one of embodiments 1 to 22”, then said embodiment refers not only toembodiments indicated by the integers such as 1 and 2 but also toembodiments indicated by numbers with a decimal component such as 22.1.

Cyano means a —CN group. Amino means an —NH₂ group. Hydroxyl or hydroxystands for an —OH group.

The presence of one or more C═N double bonds in a compound of formula(I) means that the compounds may occur in E or Z isomeric forms. Formula(I) is intended to include all those possible stereoisomeric forms andmixtures thereof.

The presence of one or more possible asymmetric carbon atoms in acompound of formula (I) means that the compounds may occur in opticallystereoisomeric forms, i.e. enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formula (I) is intended to include all those possiblestereoisomeric forms and mixtures thereof. The present inventionincludes all those possible stereoisomeric forms and mixtures thereoffor a compound of formula (I). Likewise, formula (I) is intended toinclude all possible tautomers. The present invention includes allpossible tautomeric forms for a compound of formula (I).

In each case, the compounds of formula (I) according to the inventionare in free form, in oxidized form as an N-oxide or in salt form, e.g.an agronomically usable salt form.

Embodiment 2: A compound according to embodiment 1, wherein Ar¹ and Ar²are independently of each other phenyl, thienyl, pyridyl, pyrimidinyl,pyrazinyl, pyridazinyl, furanyl, wherein said phenyl, thienyl, pyridyl,pyrimidinyl, pyrazinyl, pyridazinyl, furanyl is unsubstituted orsubstituted by one to three substituents independently selected fromC₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃₋₈cycloalkylC₀₋₆alkyl,C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl,C₃₋₈halocycloalkylC₀₋₆alkyl, C₁-C₃haloalkyl-C₃-C₆cycloalkyl,heterocyclylC₀₋₆alkyl, halogen, cyano, cyano-C₁-C₄alkyl,cyano-C₃-C₆cycloalkyl, nitro, C₁-C₆alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkoxy-C₁-C₄alkyl, —S—C₁-C₆alkyl, —S(O)—C₁-C₆alkyl, —S(═O)₂C₁-C₆alkyl, —S(═O)(═NH)C₁-C₆alkyl, C₁-C₆alkylamino, C₂-C₆dialkylamino,C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino,C₁-C₆alkylcarbonyl, CHO, C₁-C₆alkoxycarbonyl, C₂-C₆haloalkoxycarbonyl,C₁-C₆alkylaminocarbonyl, C₁-C₆haloalkylaminocarbonyl and C₁-C₄dialkylaminocarbonyl.

Embodiment 3: A compound according to embodiment 1 or 2, wherein Ar¹ isphenyl which is unsubstituted or substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, heterocyclylC₀₋₆alkyl, halogen, cyano,nitro, C₁-C₆alkoxy, C₁-C₆haloalkoxy, —S—C₁-C₆alkyl, —S(O)—C₁-C₆alkyl,—S(═O)₂ C₁-C₆alkyl, —S(═O)(═NH)C₁-C₆alkyl, C₂-C₆alkylcarbonyl, CHO,C₂-C₆alkoxycarbonyl and C₂-C₆haloalkoxycarbonyl.

Embodiment 4: A compound according to any one of embodiments 1 to 3,wherein Ar¹ is phenyl which is unsubstituted or substituted by one tothree substituents independently selected from C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, C₁-C₆alkoxyand C₁-C₆haloalkoxy.

Embodiment 4.1: A compound according to any one of embodiments 1 to 3,wherein Ar¹ is unsubstituted phenyl.

Embodiment 5: A compound according to any one of embodiments 1 to 4,wherein Ar² is phenyl which is unsubstituted or substituted by one tothree substituents independently selected from C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, cyano,C₁-C₆alkoxy, C₁-C₆haloalkoxy and —S— C₁-C₆alkyl.

Embodiment 6: A compound according to any one of embodiments 1 to 5,wherein Ar² is phenyl which is unsubstituted or substituted by one tothree substituents independently selected from C₁-C₄alkyl,C₁-C₄haloalkyl, halogen, C₁-C₄alkoxy and C₁-C₄haloalkoxy.

Embodiment 7: A compound according to any one of embodiments 1 to 6,wherein X¹ is O or NR⁶; R⁶ is selected from hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, halo-C₃-C₆cycloalkyl, C₂-C₆alkenyl,C₂-C₆haloalkenyl, C₂-C₆-alkynyl, C₂-C₆haloalkynyl,C₁-C₆alkoxy-C₁-C₆alkyl, —S—C₁-C₆alkyl, —S(O)—C₁-C₆alkyl, —S(═O)₂C₁-C₆alkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl,C₁-C₆alkoxycarbonyloxy, C₁-C₆alkylaminocarbonyloxy,C₁-C₆dialkylaminocarbonyloxy and —C(═N—C₁-C₄alkoxy)-C₁-C₄alkyl;preferably R⁶ is hydrogen or C₁-C₆alkyl; more preferably R⁶ is hydrogenor C₁-C₃alkyl; most preferably R⁶ is hydrogen or methyl.

Embodiment 8: A compound according to any one of embodiments 1 to 7,wherein X² is a bond or (CR⁴R⁵)_(n); n is 1 or 2; R⁴ and R⁵ areindependently selected from hydrogen, C₁-C₆alkyl, halo-C₁-C₆alkyl,C₃-C₆cycloalkyl and C₁-C₆alkoxy; preferably R⁴ and R⁵ are independentlyselected from hydrogen and C₁-C₆alkyl.

Embodiment 9: A compound according to any one of embodiments 1 to 7,wherein X² is a bond.

Embodiment 10: A compound according to any one of embodiments 1 to 9,wherein W is O or NR²; R² is selected from hydrogen, C₁-C₆alkyl,C₁-C₆haloalkyl, C₃-C₆cycloalkyl, halo-C₃-C₆cycloalkyl, C₂-C₆alkenyl,C₂-C₆haloalkenyl, C₂-C₆-alkynyl, C₂-C₆haloalkynyl,C₁-C₆alkoxy-C₁-C₆alkyl, S—C₆-C₆alkyl, —S(O)—C₁-C₆alkyl, —S(═O)₂C₁-C₆alkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylaminocarbonyl, C₁-C₆dialkylaminocarbonyl,C₁-C₆alkoxycarbonyloxy, C₁-C₆alkylaminocarbonyloxy,C₁-C₆dialkylaminocarbonyloxy and —C(═N—C₁-C₄alkoxy)-C₁-C₄alkyl,preferably R² is hydrogen or C₁-C₆alkyl; more preferably R² is hydrogenor C₁-C₃alkyl; most preferably R² is hydrogen or methyl.

Embodiment 11: A compound according to any one of embodiments 1 to 9,wherein R¹ is hydrogen, C₁-C₆-alkyl, C₁-C₆haloalkyl, C₃-C₆-cycloalkyl orC₁-C₆-alkoxy; preferably, R¹ is hydrogen or C₁-C₆-alkyl; morepreferably, R¹ is hydrogen or C₁-C₃-alkyl; most preferably R¹ ishydrogen or methyl.

Embodiment 12: A compound according to any one of embodiments 1 to 11,wherein R^(y) is hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₃-alkoxy; preferably, R^(y) is C₁-C₆-alkyl; morepreferably, R^(y) is C₁-C₃-alkyl; most preferably R^(y) is methyl.

Embodiment 13: A compound according to any one of embodiments 1 to 12,wherein J is a group selected from J^(1′) to J¹²:

wherein n is 0, 1 or 2 and R²⁰ is independently selected from hydrogen,C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, C₁-C₆alkoxy,and C₁-C₆haloalkoxy.

Embodiment 14: A compound according to any one of embodiments 1 to 12,wherein J is selected from:

more preferably J is selected from:

most preferably J is

Embodiment 15: A compound according to any one of embodiments 1 to 14,of formula (I)

wherein

Ar¹ is phenyl which is unsubstituted or substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₃-C₆halocycloalkyl, C₁-C₃haloalkyl-C₃-C₆cycloalkyl,C₃-C₆cycloalkoxy, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy;

Ar² is phenyl which is unsubstituted or substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, cyano,C₁-C₆alkoxy, C₁-C₆haloalkoxy and —S—C₁-C₆alkyl;

X¹ is O or NR⁶;

X² is a bond, —CH₂— or —CH₂CH₂—;

W is O or NR²;

Y is oxygen or sulfur;

R¹ is hydrogen or C₁-C₆alkyl;

R² is selected from hydrogen, C₁-C₆alkyl and C₁-C₆haloalkyl;

R³ is selected from hydrogen, C₁-C₆alkyl and C₁-C₆haloalkyl;

R⁶ is hydrogen or C₁-C₆alkyl;

J is a group selected from J^(1′), J^(2′), J^(3′), J⁹ and J¹¹:

wherein n is 0, 1 or 2, and R²⁰ is independently selected from hydrogen,C₃-C₆halocycloalkyl and C₁-C₆haloalkoxy;

R^(y) is C₁-C₆alkyl; or

J and R^(y) together with the carbon atom to which they are attachedform a bicyclic ring of formula

q is 1 or 2;

R¹⁶ and R¹⁷ are independently selected from hydrogen,C₃-C₆halocycloalkyl and C₁-C₆haloalkoxy; or an agrochemically acceptablesalt, stereoisomer, tautomer, N-oxide thereof.

Embodiment 16: A compound according to any one of embodiments 1 to 15,of formula (I)

wherein

Ar¹ is phenyl which is unsubstituted or substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₃-C₆cycloalkyl,C₁-C₆haloalkyl, C₃-C₆halocycloalkyl, C₁-C₃haloalkyl-C₃-C₆cycloalkyl,C₃-C₆cycloalkoxy, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy;

Ar² is phenyl which is unsubstituted or substituted by one to threesubstituents independently selected from C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, cyano,C₁-C₆alkoxy, C₁-C₆haloalkoxy and —S—C₁-C₆alkyl;

X¹ is O or NR⁶;

X² is a bond, —CH₂— or —CH₂CH₂—;

W is O or NR²;

Y is oxygen or sulfur;

R¹ is hydrogen or C₁-C₆alkyl;

R² is selected from hydrogen, C₁-C₆alkyl and C₁-C₆haloalkyl;

R³ is selected from hydrogen, C₁-C₆alkyl and C₁-C₆haloalkyl;

R⁶ is hydrogen or C₁-C₆alkyl;

J is a group selected from J^(1′), J^(2′), J^(3′), J⁹ and J¹¹:

wherein n is 0, 1 or 2, and R²⁰ is independently selected from hydrogen,C₃-C₆halocycloalkyl and C₁-C₆haloalkoxy;

R^(y) is C₁-C₆alkyl;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Embodiment 17: A compound according to any one of embodiments 1 to 16,of formula (Ia)

or formula (Ib)

wherein

R^(a), R^(b) and R^(c) are independently selected from hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy;

X¹ is O or NR⁶;

X² is a bond, —CH₂— or —CH₂CH₂—;

W is O or NR²;

Y is oxygen or sulfur;

R¹ is hydrogen or methyl;

R² is hydrogen or C₁-C₆alkyl;

R⁶ is hydrogen or C₁-C₆alkyl;

R¹⁶ is C₁-C₆haloalkoxy;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Embodiment 18: A compound according to any one of embodiments 1 to 17,of formula (Ia)

wherein

R^(a), R^(b) and R^(c) are independently selected from hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy;

X¹ is O or NR⁶;

X² is a bond, —CH₂— or —CH₂CH₂—;

W is O or NR²;

Y is oxygen or sulfur;

R¹ is hydrogen or methyl;

R² is hydrogen or C₁-C₆alkyl;

R⁶ is hydrogen or C₁-C₆alkyl;

R¹⁶ is C₁-C₆haloalkoxy;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Embodiment 19: A compound according to any one of embodiments 1 to 18,of formula (Ia)

wherein

R^(a) is R^(b) and R^(c) are independently selected from hydrogen,methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxy and —OCF₃;

X¹ is selected from O, NH and NCH₃;

X² is a bond;

W is selected from O, NH and NCH₃;

Y is oxygen or sulfur;

R¹ is hydrogen or methyl;

R¹⁶ is —OCF₃ or —OCF₂CF₃;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Embodiment 20: A compound according to any one of embodiments 1 to 17,of formula (Ib)

wherein

R^(a), R^(b) and R^(c) are independently selected from hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy;

X¹ is O or NR⁶;

X² is a bond, —CH₂— or —CH₂CH₂—;

W is O or NR²;

Y is oxygen or sulfur;

R¹ is hydrogen or methyl;

R² is hydrogen or C₁-C₆alkyl;

R⁶ is hydrogen or C₁-C₆alkyl;

R¹⁶ is C₁-C₆haloalkoxy;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

Embodiment 21: A compound according to any one of embodiments 1 to 17,of formula (Ib)

wherein

R^(a) is R^(b) and R^(c) are independently selected from hydrogen,methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxy and —OCF₃;

X¹ is selected from O, NH and NCH₃;

X² is a bond;

W is selected from O, NH and NCH₃;

Y is oxygen or sulfur;

R¹ is hydrogen or methyl;

R¹⁶ is —OCF₃ or —OCF₂CF₃;

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.

The compounds according to any one of embodiments 1 to 21 may beprepared according to the following Schemes 1 to 14.

Compounds of formula (II) can be prepared, as depicted in scheme 1, byreacting compounds of formula (II) with compounds of formula (III), inthe presence or in the absence of a base such as triethylamine orN,N-diisopropylethylamine, in a solvent or a solvent mixture, like, fortetrahydrofuran, DMF, dioxane or acetonitrile. The reaction temperaturecan preferentially range from room temperature to the boiling point ofthe reaction mixture. In formula (I), (II) and (III), J, R^(y), X¹, Ar¹,X², R¹, W, Y and Ar₂ are as described above.

Compounds of formula (IIa) can be prepared, as depicted in scheme 2, byreacting compounds of formula (IVa) with compounds of formula (V), bymethods known to those skilled in the art (see e.g. M. Smith, J. March,March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).Compounds of formula (V) can be prepared by methods known to thoseskilled in the art (see e.g. M. Smith, J. March, March's AdvancedOrganic Chemistry, 6^(th) edition, Wiley, 2007). In formula (IIa), (IVa)and (V), W is NR² and J, R^(y), X¹, Ar¹, X², R¹, Y and Ar₂ are asdescribed above.

Compounds of formula (IIb) can be prepared, as depicted in scheme 3, byreacting compounds of formula (IVb) with compounds of formula (V), bymethods known to those skilled in the art (see e.g. M. Smith, J. March,March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).Compounds of formula (V) can be prepared by methods known to thoseskilled in the art (see e.g. M. Smith, J. March, March's AdvancedOrganic Chemistry, 6^(th) edition, Wiley, 2007). In formula (lib), (IVb)and (V), W is O and J, R^(y), X¹, Ar¹, X², R¹, Y and Ar₂ are asdescribed above.

Compounds of formula (IVa) can be prepared, as depicted in scheme 4, byreacting compounds of formula (VI) with compounds of formula (VIIa), bymethods known to those skilled in the art (see e.g. M. Smith, J. March,March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).Compounds of formula (VIIa) can be prepared by methods known to thoseskilled in the art (see e.g. M. Smith, J. March, March's AdvancedOrganic Chemistry, 6^(th) edition, Wiley, 2007). In formula (IVa), (VI)and (VIIa), W is NR² and J, R^(y), X¹, Ar¹, X² and R¹ are as describedabove.

Compounds of formula (IVb) can be prepared, as depicted in scheme 5, byreacting compounds of formula (VI) with hydroxylamine (VIIb), by methodsknown to those skilled in the art (see e.g. M. Smith, J. March, March'sAdvanced Organic Chemistry, 6^(th) edition, Wiley, 2007). In formula(IVb), (VI) and (VIIb), W is O and J, R^(y), X¹, Ar¹, X² and R¹ are asdescribed above.

Compounds of formula (VI) can be prepared according to several methodsknown to those skilled in the art.

More specifically, compounds of formula (Via) can be prepared, asdepicted in scheme 6, via addition of a compound of formula R¹—M (M ise.g. MgCl, MgBr, Li, ZnCl) to a compound of formula (VIII), by methodsknown to those skilled in the art (see e.g. M. Smith, J. March, March'sAdvanced Organic Chemistry, 6^(th) edition, Wiley, 2007). In formula(Via) and (VIII), R¹ is not hydrogen and J, R^(y), X¹ and X² are asdescribed above. Compounds of formula (VIb) can be prepared, as depictedin scheme 6, via reduction of a compound of formula (VIII) (e.g. withDIBALH), by methods known to those skilled in the art (see e.g. M.Smith, J. March, March's Advanced Organic Chemistry, 6^(th) edition,Wiley, 2007). In formula (VIb) and (VIII), R¹ is hydrogen and J, R^(y),Ar¹, X¹ and X² are as described above.

Compounds of formula (VIIIa) can be prepared, as depicted in scheme 7,by reacting compounds of formula (IXa) with compounds of formula (X), inthe presence or in the absence of a base such as triethylamine orN,N-diisopropylethylamine, in a solvent or a solvent mixture, like, fortetrahydrofuran, DMF, dioxane or acetonitrile. The reaction temperaturecan preferentially range from room temperature to the boiling point ofthe reaction mixture. In formula (VIIIa), (IXa) and (X), X¹ is NR⁶ andJ, R^(y), Ar¹ and X² are as described above.

Compounds of formula (IXa) can be prepared, as depicted in scheme 8, byreacting compounds of formula (XI) with compounds of formula (XII), bymethods known to those skilled in the art (see e.g. M. Smith, J. March,March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).Compounds of formula (XII) can be prepared by methods (e.g. reduction ofthe corresponding diazonium salts) known to those skilled in the art(see e.g. M. Smith, J. March, March's Advanced Organic Chemistry, 6^(th)edition, Wiley, 2007). When X²=direct bond, compounds of formula (XII)can be prepared starting from available materials by methods (e.g.reduction of the corresponding diazonium salts) known to those skilledin the art (see e.g. M. Smith, J. March, March's Advanced OrganicChemistry, 6^(th) edition, Wiley, 2007). In formula (IXa), (XI) and(XII), J, R^(y), Ar¹ and X² are as described above.

Compounds of formula (XIIa) can be prepared, as depicted in scheme 9,from compounds of formula (XIIIa), where PG=protective group (e.g.tert-butyloxycarbonyl or benzyloxycarbonyl), by methods (e.g.deprotection followed by diazonium salts formation and in situreduction) known to those skilled in the art (see e.g. M. Smith, J.March, March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).In formula (XIIa) and (XIIIa), Ar¹ is as described above.

Compounds of formula (XIIIa) can be prepared, as depicted in scheme 10,from compounds of formula (XIVa), where PG=protective group (e.g.tert-butyloxycarbonyl or benzyloxycarbonyl), by methods (e.g.hydrogenation) known to those skilled in the art (see e.g. M. Smith, J.March, March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).In formula (XIVa) and (XIIIa), Ar¹ is as described above.

Compounds of formula (XIVa) can be prepared, as depicted in scheme 11,from compounds of formula (XVa), where PG=protective group (e.g.tert-butyloxycarbonyl or benzyloxycarbonyl), by methods (e.g. Wittigreaction) known to those skilled in the art (see e.g. M. Smith, J.March, March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).In formula (XVa) and (XIVa), Ar¹ is as described above.

Compounds of formula (VIIIb) can be prepared, as depicted in scheme 12,by reacting compounds of formula (XVI) with compounds of formula (XVII),by methods known to those skilled in the art (see e.g. M. Smith, J.March, March's Advanced Organic Chemistry, 6^(th) edition, Wiley, 2007).Compounds of formula (XVI) and (XVII) can be prepared by methods knownto those skilled in the art (see e.g. M. Smith, J. March, March'sAdvanced Organic Chemistry, 6^(th) edition, Wiley, 2007). In formula(XVII), (XVI) and (XVII), LG is a leaving group (e.g. F, NO₂), J, R^(y),Ar¹ and X² are as described above.

Compounds of formula (XVIIa) can be prepared, as depicted in scheme 13,from compounds of formula (XVIIIa) by methods (e.g. hydrogenation) knownto those skilled in the art (see e.g. M. Smith, J. March, March'sAdvanced Organic Chemistry, 6^(th) edition, Wiley, 2007). In formula(XVIIa) and (XVIIIa), LG is a leaving group (e.g. F, NO₂) and Ar¹ is asdescribed above.

Compounds of formula (XVIIIa) can be prepared, as depicted in scheme 14,from compounds of formula (XIXa), by methods (e.g. Wittig reaction)known to those skilled in the art (see e.g. M. Smith, J. March, March'sAdvanced Organic Chemistry, 6^(th) edition, Wiley, 2007). In formula(XIXa) and (XVIIIa), LG is a leaving group (e.g. F, NO₂) and Ar¹ is asdescribed above.

Depending on the procedure or the reaction conditions, the compounds offormula (I), which have salt-forming properties can be obtained in freeform or in the form of salts.

The compounds of formula (I) and, where appropriate, the tautomersthereof, in each case in free form or in salt form, can be present inthe form of one of the stereoisomers which are possible or as a mixtureof these, for example in the form of pure stereoisomers, such asantipodes and/or diastereomers, or as stereoisomer mixtures, such asenantiomer mixtures, for example racemates, diastereomer mixtures orracemate mixtures, depending on the number, absolute and relativeconfiguration of asymmetric carbon atoms which occur in the moleculeand/or depending on the configuration of non-aromatic double bonds whichoccur in the molecule; the invention relates to the pure stereoisomersand also to all stereoisomer mixtures which are possible and is to beunderstood in each case in this sense hereinabove and herein below, evenwhen stereochemical details are not mentioned specifically in each case.

Diastereomer mixtures or racemate mixtures of compounds of formula (I),in free form or in salt form, which can be obtained depending on whichstarting materials and procedures have been chosen can be separated in aknown manner into the pure diasteromers or racemates on the basis of thephysicochemical differences of the components, for example by fractionalcrystallization, distillation and/or chromatography.

Enantiomer mixtures, such as racemates, which can be obtained in asimilar manner can be resolved into the optical antipodes by knownmethods, for example by recrystallization from an optically activesolvent, by chromatography on chiral adsorbents, for examplehigh-performance liquid chromatography (HPLC) on acetyl cellulose, withthe aid of suitable microorganisms, by cleavage with specific,immobilized enzymes, via the formation of inclusion compounds, forexample using chiral crown ethers, where only one enantiomer iscomplexed, or by conversion into diastereomeric salts, for example byreacting a basic end-product racemate with an optically active acid,such as a carboxylic acid, for example camphor, tartaric or malic acid,or sulfonic acid, for example camphorsulfonic acid, and separating thediastereomer mixture which can be obtained in this manner, for exampleby fractional crystallization based on their differing solubilities, togive the diastereomers, from which the desired enantiomer can beresolved by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained not only by separatingsuitable stereoisomer mixtures, but also by generally known methods ofdiastereoselective or enantioselective synthesis, for example bycarrying out the process according to the invention with startingmaterials of a suitable stereochemistry.

N-oxides can be prepared by reacting a compound of the formula (I) witha suitable oxidizing agent, for example the H₂O₂/urea adduct in thepresence of an acid anhydride, e.g. trifluoroacetic anhydride. Suchoxidations are known from the literature, for example from J. Med. Chem.1989, 32, 2561 or WO 2000/15615.

The compounds of formula (I) and, where appropriate, the tautomersthereof, in each case in free form or in salt form, can, if appropriate,also be obtained in the form of hydrates and/or include other solvents,for example those which may have been used for the crystallization ofcompounds which are present in solid form.

Embodiment 22: Compounds of formula (I) according to any one ofembodiments 1 to 21 are illustrated in the following Tables 1 to 48:

Each of Tables 1 to 24, which follows the Table A below, comprises 324compounds of the formula (Ia) in which X¹, W, R^(a), R^(b) and R^(c)have the values given in each row in Table A, and X², R¹, Y and R¹⁶ havethe values given in the relevant Tables 1 to 24. Thus for instancecompound 1.001 corresponds to a compound of formula (Ia) where X¹, W,R^(a), R^(b) and R^(c) are as defined in row 1 of Table A and where X²,R¹, Y and R¹⁶ are as defined in Table 1; compound 10.123 corresponds toa compound of formula (I) where X¹, W, R^(a), R^(b) and R^(c) are asdefined in row 123 of Table A and where X², R¹, Y and R¹⁶ are as definedin Table 10.

TABLE A Table A X¹ W R^(a) R^(b) R^(c) 1 O O CH₃ CH₃ H 2 NH O CH₃ CH₃ H3 NCH₃ O CH₃ CH₃ H 4 O NH CH₃ CH₃ H 5 NH NH CH₃ CH₃ H 6 NCH₃ NH CH₃ CH₃H 7 O NCH₃ CH₃ CH₃ H 8 NH NCH₃ CH₃ CH₃ H 9 NCH₃ NCH₃ CH₃ CH₃ H 10 O OiPr CH₃ H 11 NH O iPr CH₃ H 12 NCH₃ O iPr CH₃ H 13 O NH iPr CH₃ H 14 NHNH iPr CH₃ H 15 NCH₃ NH iPr CH₃ H 16 O NCH₃ iPr CH₃ H 17 NH NCH₃ iPr CH₃H 18 NCH₃ NCH₃ iPr CH₃ H 19 O O Cl CH₃ H 20 NH O Cl CH₃ H 21 NCH₃ O ClCH₃ H 22 O NH Cl CH₃ H 23 NH NH Cl CH₃ H 24 NCH₃ NH Cl CH₃ H 25 O NCH₃Cl CH₃ H 26 NH NCH₃ Cl CH₃ H 27 NCH₃ NCH₃ Cl CH₃ H 28 O O CH₃ H H 29 NHO CH₃ H H 30 NCH₃ O CH₃ H H 31 O NH CH₃ H H 32 NH NH CH₃ H H 33 NCH₃ NHCH₃ H H 34 O NCH₃ CH₃ H H 35 NH NCH₃ CH₃ H H 36 NCH₃ NCH₃ CH₃ H H 37 O OiPr H H 38 NH O iPr H H 39 NCH₃ O iPr H H 40 O NH iPr H H 41 NH NH iPr HH 42 NCH₃ NH iPr H H 43 O NCH₃ iPr H H 44 NH NCH₃ iPr H H 45 NCH₃ NCH₃iPr H H 46 O O Cl H H 47 NH O Cl H H 48 NCH₃ O Cl H H 49 O NH Cl H H 50NH NH Cl H H 51 NCH₃ NH Cl H H 52 O NCH₃ Cl H H 53 NH NCH₃ Cl H H 54NCH₃ NCH₃ Cl H H 55 O O CH₃ Cl H 56 NH O CH₃ Cl H 57 NCH₃ O CH₃ Cl H 58O NH CH₃ Cl H 59 NH NH CH₃ Cl H 60 NCH₃ NH CH₃ Cl H 61 O NCH₃ CH₃ Cl H62 NH NCH₃ CH₃ Cl H 63 NCH₃ NCH₃ CH₃ Cl H 64 O O iPr Cl H 65 NH O iPr ClH 66 NCH₃ O iPr Cl H 67 O NH iPr Cl H 68 NH NH iPr Cl H 69 NCH₃ NH iPrCl H 70 O NCH₃ iPr Cl H 71 NH NCH₃ iPr Cl H 72 NCH₃ NCH₃ iPr Cl H 73 O OCl Cl H 74 NH O Cl Cl H 75 NCH₃ O Cl Cl H 76 O NH Cl Cl H 77 NH NH Cl ClH 78 NCH₃ NH Cl Cl H 79 O NCH₃ Cl Cl H 80 NH NCH₃ Cl Cl H 81 NCH₃ NCH₃Cl Cl H 82 O O CH₃ F H 83 NH O CH₃ F H 84 NCH₃ O CH₃ F H 85 O NH CH₃ F H86 NH NH CH₃ F H 87 NCH₃ NH CH₃ F H 88 O NCH₃ CH₃ F H 89 NH NCH₃ CH₃ F H90 NCH₃ NCH₃ CH₃ F H 91 O O iPr F H 92 NH O iPr F H 93 NCH₃ O iPr F H 94O NH iPr F H 95 NH NH iPr F H 96 NCH₃ NH iPr F H 97 O NCH₃ iPr F H 98 NHNCH₃ iPr F H 99 NCH₃ NCH₃ iPr F H 100 O O Cl F H 101 NH O Cl F H 102NCH₃ O Cl F H 103 O NH Cl F H 104 NH NH Cl F H 105 NCH₃ NH Cl F H 106 ONCH₃ Cl F H 107 NH NCH₃ Cl F H 108 NCH₃ NCH₃ Cl F H 109 O O CH₃ CH₃ OCH₃110 NH O CH₃ CH₃ OCH₃ 111 NCH₃ O CH₃ CH₃ OCH₃ 112 O NH CH₃ CH₃ OCH₃ 113NH NH CH₃ CH₃ OCH₃ 114 NCH₃ NH CH₃ CH₃ OCH₃ 115 O NCH₃ CH₃ CH₃ OCH₃ 116NH NCH₃ CH₃ CH₃ OCH₃ 117 NCH₃ NCH₃ CH₃ CH₃ OCH₃ 118 O O iPr CH₃ OCH₃ 119NH O iPr CH₃ OCH₃ 120 NCH₃ O iPr CH₃ OCH₃ 121 O NH iPr CH₃ OCH₃ 122 NHNH iPr CH₃ OCH₃ 123 NCH₃ NH iPr CH₃ OCH₃ 124 O NCH₃ iPr CH₃ OCH₃ 125 NHNCH₃ iPr CH₃ OCH₃ 126 NCH₃ NCH₃ iPr CH₃ OCH₃ 127 O O Cl CH₃ OCH₃ 128 NHO Cl CH₃ OCH₃ 129 NCH₃ O Cl CH₃ OCH₃ 130 O NH Cl CH₃ OCH₃ 131 NH NH ClCH₃ OCH₃ 132 NCH₃ NH Cl CH₃ OCH₃ 133 O NCH₃ Cl CH₃ OCH₃ 134 NH NCH₃ ClCH₃ OCH₃ 135 NCH₃ NCH₃ Cl CH₃ OCH₃ 136 O O CH₃ H OCH₃ 137 NH O CH₃ HOCH₃ 138 NCH₃ O CH₃ H OCH₃ 139 O NH CH₃ H OCH₃ 140 NH NH CH₃ H OCH₃ 141NCH₃ NH CH₃ H OCH₃ 142 O NCH₃ CH₃ H OCH₃ 143 NH NCH₃ CH₃ H OCH₃ 144 NCH₃NCH₃ CH₃ H OCH₃ 145 O O iPr H OCH₃ 146 NH O iPr H OCH₃ 147 NCH₃ O iPr HOCH₃ 148 O NH iPr H OCH₃ 149 NH NH iPr H OCH₃ 150 NCH₃ NH iPr H OCH₃ 151O NCH₃ iPr H OCH₃ 152 NH NCH₃ iPr H OCH₃ 153 NCH₃ NCH₃ iPr H OCH₃ 154 OO Cl H OCH₃ 155 NH O Cl H OCH₃ 156 NCH₃ O Cl H OCH₃ 157 O NH Cl H OCH₃158 NH NH Cl H OCH₃ 159 NCH₃ NH Cl H OCH₃ 160 O NCH₃ Cl H OCH₃ 161 NHNCH₃ Cl H OCH₃ 162 NCH₃ NCH₃ Cl H OCH₃ 163 O O CH₃ Cl OCH₃ 164 NH O CH₃Cl OCH₃ 165 NCH₃ O CH₃ Cl OCH₃ 166 O NH CH₃ Cl OCH₃ 167 NH NH CH₃ ClOCH₃ 168 NCH₃ NH CH₃ Cl OCH₃ 169 O NCH₃ CH₃ Cl OCH₃ 170 NH NCH₃ CH₃ ClOCH₃ 171 NCH₃ NCH₃ CH₃ Cl OCH₃ 172 O O iPr Cl OCH₃ 173 NH O iPr Cl OCH₃174 NCH₃ O iPr Cl OCH₃ 175 O NH iPr Cl OCH₃ 176 NH NH iPr Cl OCH₃ 177NCH₃ NH iPr Cl OCH₃ 178 O NCH₃ iPr Cl OCH₃ 179 NH NCH₃ iPr Cl OCH₃ 180NCH₃ NCH₃ iPr Cl OCH₃ 181 O O Cl Cl OCH₃ 182 NH O Cl Cl OCH₃ 183 NCH₃ OCl Cl OCH₃ 184 O NH Cl Cl OCH₃ 185 NH NH Cl Cl OCH₃ 186 NCH₃ NH Cl ClOCH₃ 187 O NCH₃ Cl Cl OCH₃ 188 NH NCH₃ Cl Cl OCH₃ 189 NCH₃ NCH₃ Cl ClOCH₃ 190 O O CH₃ F OCH₃ 191 NH O CH₃ F OCH₃ 192 NCH₃ O CH₃ F OCH₃ 193 ONH CH₃ F OCH₃ 194 NH NH CH₃ F OCH₃ 195 NCH₃ NH CH₃ F OCH₃ 196 O NCH₃ CH₃F OCH₃ 197 NH NCH₃ CH₃ F OCH₃ 198 NCH₃ NCH₃ CH₃ F OCH₃ 199 O O iPr FOCH₃ 200 NH O iPr F OCH₃ 201 NCH₃ O iPr F OCH₃ 202 O NH iPr F OCH₃ 203NH NH iPr F OCH₃ 204 NCH₃ NH iPr F OCH₃ 205 O NCH₃ iPr F OCH₃ 206 NHNCH₃ iPr F OCH₃ 207 NCH₃ NCH₃ iPr F OCH₃ 208 O O Cl F OCH₃ 209 NH O Cl FOCH₃ 210 NCH₃ O Cl F OCH₃ 211 O NH Cl F OCH₃ 212 NH NH Cl F OCH₃ 213NCH₃ NH Cl F OCH₃ 214 O NCH₃ Cl F OCH₃ 215 NH NCH₃ Cl F OCH₃ 216 NCH₃NCH₃ Cl F OCH₃ 217 O O CH₃ CH₃ CF₃ 218 NH O CH₃ CH₃ CF₃ 219 NCH₃ O CH₃CH₃ CF₃ 220 O NH CH₃ CH₃ CF₃ 221 NH NH CH₃ CH₃ CF₃ 222 NCH₃ NH CH₃ CH₃CF₃ 223 O NCH₃ CH₃ CH₃ CF₃ 224 NH NCH₃ CH₃ CH₃ CF₃ 225 NCH₃ NCH₃ CH₃ CH₃CF₃ 226 O O iPr CH₃ CF₃ 227 NH O iPr CH₃ CF₃ 228 NCH₃ O iPr CH₃ CF₃ 229O NH iPr CH₃ CF₃ 230 NH NH iPr CH₃ CF₃ 231 NCH₃ NH iPr CH₃ CF₃ 232 ONCH₃ iPr CH₃ CF₃ 233 NH NCH₃ iPr CH₃ CF₃ 234 NCH₃ NCH₃ iPr CH₃ CF₃ 235 OO Cl CH₃ CF₃ 236 NH O Cl CH₃ CF₃ 237 NCH₃ O Cl CH₃ CF₃ 238 O NH Cl CH₃CF₃ 239 NH NH Cl CH₃ CF₃ 240 NCH₃ NH Cl CH₃ CF₃ 241 O NCH₃ Cl CH₃ CF₃242 NH NCH₃ Cl CH₃ CF₃ 243 NCH₃ NCH₃ Cl CH₃ CF₃ 244 O O CH₃ H CF₃ 245 NHO CH₃ H CF₃ 246 NCH3 O CH₃ H CF₃ 247 O NH CH₃ H CF₃ 248 NH NH CH₃ H CF₃249 NCH₃ NH CH₃ H CF₃ 250 O NCH₃ CH₃ H CF₃ 251 NH NCH₃ CH₃ H CF₃ 252NCH₃ NCH₃ CH₃ H CF₃ 253 O O iPr H CF₃ 254 NH O iPr H CF₃ 255 NCH₃ O iPrH CF₃ 256 O NH iPr H CF₃ 257 NH NH iPr H CF₃ 258 NCH₃ NH iPr H CF₃ 259 ONCH₃ iPr H CF₃ 260 NH NCH₃ iPr H CF₃ 261 NCH₃ NCH₃ iPr H CF₃ 262 O O ClH CF₃ 263 NH O Cl H CF₃ 264 NCH₃ O Cl H CF₃ 265 O NH Cl H CF₃ 266 NH NHCl H CF₃ 267 NCH₃ NH Cl H CF₃ 268 O NCH₃ Cl H CF₃ 269 NH NCH₃ Cl H CF₃270 NCH₃ NCH₃ Cl H CF₃ 271 O O CH₃ Cl CF₃ 272 NH O CH₃ Cl CF₃ 273 NCH₃ OCH₃ Cl CF₃ 274 O NH CH₃ Cl CF₃ 275 NH NH CH₃ Cl CF₃ 276 NCH₃ NH CH₃ ClCF₃ 277 O NCH₃ CH₃ Cl CF₃ 278 NH NCH₃ CH₃ Cl CF₃ 279 NCH3 NCH₃ CH₃ ClCF₃ 280 O O iPr Cl CF₃ 281 NH O iPr Cl CF₃ 282 NCH₃ O iPr Cl CF₃ 283 ONH iPr Cl CF₃ 284 NH NH iPr Cl CF₃ 285 NCH₃ NH iPr Cl CF₃ 286 O NCH₃ iPrCl CF₃ 287 NH NCH₃ iPr Cl CF₃ 288 NCH₃ NCH₃ iPr Cl CF₃ 289 O O Cl Cl CF₃290 NH O Cl Cl CF₃ 291 NCH₃ O Cl Cl CF₃ 292 O NH Cl Cl CF₃ 293 NH NH ClCl CF₃ 294 NCH₃ NH Cl Cl CF₃ 295 O NCH₃ Cl Cl CF₃ 296 NH NCH₃ Cl Cl CF₃297 NCH₃ NCH₃ Cl Cl CF₃ 298 O O CH₃ F CF₃ 299 NH O CH₃ F CF₃ 300 NCH₃ OCH₃ F CF₃ 301 O NH CH₃ F CF₃ 302 NH NH CH₃ F CF₃ 303 NCH₃ NH CH₃ F CF₃304 O NCH₃ CH₃ F CF₃ 305 NH NCH₃ CH₃ F CF₃ 306 NCH₃ NCH₃ CH₃ F CF₃ 307 OO iPr F CF₃ 308 NH O iPr F CF₃ 309 NCH3 O iPr F CF₃ 310 O NH iPr F CF₃311 NH NH iPr F CF₃ 312 NCH₃ NH iPr F CF₃ 313 O NCH₃ iPr F CF₃ 314 NHNCH₃ iPr F CF₃ 315 NCH₃ NCH₃ iPr F CF₃ 316 O O Cl F CF₃ 317 NH O Cl FCF₃ 318 NCH₃ O Cl F CF₃ 319 O NH Cl F CF₃ 320 NH NH Cl F CF₃ 321 NCH₃ NHCl F CF₃ 322 O NCH₃ Cl F CF₃ 323 NH NCH₃ Cl F CF₃ 324 NCH₃ NCH₃ Cl F CF₃Table 1:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is H, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) areas defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 2:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is H, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 3:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is CH₃, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 4:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is CH₃, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A.

Table 5:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is H, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) areas defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 6:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is H, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 7:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is CH₃, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 8:

There are provided 324 of formula Ia wherein X² is CH₂CH₂, R¹ is CH₃, Yis S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 9:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is H, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 10:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is H, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 11:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is CH₃, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) andR^(c) are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 12:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is CH₃, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 13:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is H, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 14:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is H, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 15:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is CH₃, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) andR^(c) are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 16:

There are provided 324 compounds of formula Ia wherein X² is CH₂CH₂, R¹is CH₃, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 17:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isH, Y is O, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined in TableA; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 18:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isCH3, Y is O, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 19:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isH, Y is S, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined in TableA; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 20:

There are provided 324 of formula Ia wherein X2 is CH2, R1 is CH3, Y isS, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined in Table A; or anagrochemically acceptable salt, stereoisomer, tautomer, N-oxidesthereof.

Table 21:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isH, Y is O, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 22:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isCH3, Y is O, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 23:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isH, Y is S, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 24:

There are provided 324 compounds of formula Ia wherein X2 is CH2, R1 isCH3, Y is S, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Each of Tables 25 to 48 below comprises 324 compounds of the formula(Ib) in which X¹, W, R^(a), R^(b) and R^(c) have the values given ineach row in Table A, and X², R¹, Y and R¹⁶ have the values given in therelevant Tables 25 to 48. Thus for instance compound 1.025 correspondsto a compound of formula (Ib) where X¹, W, R^(a), R^(b) and R^(c) are asdefined in row 1 of Table A and where X², R¹, Y and R¹⁶ are as definedin Table 25; compound 123.042 corresponds to a compound of formula (Ib)where X¹, W, R^(a), R^(b) and R^(c) are as defined in row 123 of Table Aand where X², R¹, Y and R¹⁶ are as defined in Table 42.

Table 25:

There are provided 324 compounds of formula Ia wherein X² is directbond, R¹ is H, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) areas defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 26:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is H, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 27:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is CH₃, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 28:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is CH₃, Y is O, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 29:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is H, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) areas defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 30:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is H, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 31:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is CH₃, Y is S, R¹⁶ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 32:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is CH₃, Y is S, R¹ is OCF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 33:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is H, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 34:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is H, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 35:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is CH₃, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) andR^(c) are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 36:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is CH₃, Y is O, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 37:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is H, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c)are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 38:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is H, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 39:

There are provided 324 compounds of formula Ib wherein X² is directbond, R¹ is CH₃, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) andR^(c) are as defined in Table A; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxides thereof.

Table 40:

There are provided 324 compounds of formula Ib wherein X² is CH₂CH₂, R¹is CH₃, Y is S, R¹⁶ is OCF₂CF₃ and X¹, W, R^(a), R^(b) and R^(c) are asdefined in Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 41:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is H, Y is O, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 42:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is CH3, Y is O, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 43:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is H, Y is S, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined inTable A.

Table 44:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is CH3, Y is S, R16 is OCF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 45:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is H, Y is O, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 46:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is CH3, Y is O, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as definedin Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Table 47:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is H, Y is S, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as defined inTable A; or an agrochemically acceptable salt, stereoisomer, tautomer,N-oxides thereof.

Table 48:

There are provided 324 compounds of formula Ib wherein X2 is CH2CH2, R1is CH3, Y is S, R16 is OCF2CF3 and X1, W, Ra, Rb and Rc are as definedin Table A; or an agrochemically acceptable salt, stereoisomer,tautomer, N-oxides thereof.

Embodiment 22.1: A compound according to embodiment 1, wherein thecompound is selected from

Example No. Structures IUPAC Name 1

1-(2,6-dimethylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methylene- amino]urea 2

[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methyleneamino] N-(2,6-dimethylphenyl) carbamate 3

1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 4

1-(2-isopropylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methylene- amino]urea 5

1-(2-isopropylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methylene- amino]thiourea 6

1-(2-isopropylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]urea 7

1-(2,6-dimethylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]urea 8

1-(2-isopropylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]thiourea 9

1-(2,6-dimethylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methylene- amino]thiourea 10

1-(2,6-dimethylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]thiourea 11

1-(2,6-dimethylphenyl)-3-[[4-[2-[5- (trifluoromethoxy)indan-1-ylidene]hydrazino]phenyl]methylene- amino]thiourea 12

[[4-[2-[1-[4- (trifluoromethyl)phenyl]ethylidene]hydrazino]phenyl]methyleneamino] N-(2,6- dimethylphenyl)carbamate 13

1-(2-isopropylphenyl)-3-[[4-[2-[1- [3-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]urea 14

1-(2-isopropylphenyl)-3-[[4-[2-[1- [3-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 15

1-(2,6-dimethylphenyl)-3-[[4-[2-[1- [3-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methylene- amino]urea 16

1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[3-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 17

1-(2-isopropylphenyl)-3-[[4-[2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]urea 18

1-(2,6-dimethylphenyl)-3-[[4-[2-[1- [2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 19

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]urea 20

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 21

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]urea 22

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 23

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 24

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]urea 25

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]urea 26

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]thiourea 27

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]urea 28

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]thiourea 29

1-[[4-[2-[1-[4- (difluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]- 3-(2,6-dimethylphenyl)urea 30

1-[[4-[[5-(trifluoromethoxy)indan-1- ylidene]amino]oxyphenyl]methylene-amino]-3-[2- (trifluoromethyl)phenyl]thiourea 31

1-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]-3-[2- (trifluoromethyl)phenyl]thioureaor an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidesthereof.

The compounds according to any one of embodiments 1 to 22 arepreventively and/or curatively valuable active ingredients in the fieldof pest control, even at low rates of application, which have afavorable biocidal spectrum and are well tolerated by warm-bloodedspecies, fish and plants. Compounds according to any one of embodiments1 to 22 may act against all or only individual developmental stages ofnormally sensitive, but also resistant, animal pests, such as insects orrepresentatives of the order Acarina. The insecticidal or acaricidalactivity of the compounds can manifest itself directly, i. e. indestruction of the pests, which takes place either immediately or onlyafter some time has elapsed, for example during ecdysis, or indirectly,for example in a reduced oviposition and/or hatching rate, a goodactivity corresponding to a destruction rate (mortality) of at least 50to 60%.

Examples of the abovementioned animal pests are:

from the order Acarina, for example, Acalitus spp, Aculus spp,Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp.,Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp,Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp.,Ixodes spp., Olygonychus spp, Ornithodoros spp., Polyphagotarsone latus,Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp,Polypha-gotarsonemus spp, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp.and Tetranychus spp.;

from the order Anoplura, for example, Haematopinus spp., Linognathusspp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Coleoptera, for example, Agriotes spp., Amphimallonmajale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylusatromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis,Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculiospp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderusabderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemushampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp.,Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp,Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilusspp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popilliaspp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp.,Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp,Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp.and Trogoderma spp.;

from the order Diptera, for example, Aedes spp., Anopheles spp,Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp,Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp.,Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fanniaspp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypodermaspp., Hyppobosca spp., Liriomy-za spp., Lucilia spp., Melanagromyzaspp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyiahyoscyami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata,Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. andTipula spp.;

from the order Hemiptera, for example, Acanthocoris scabrator,Acrosternum spp, Adelphocoris lineolatus, Amblypelta nitida, Bathycoeliathalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis,Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercusspp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp.,Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp,Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoristenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp.,Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophara spp., Thyanta spp, Triatoma spp., and Vatigailludens;

from the order homoptera, for example, Acyrthosium pisum, Adalges spp,Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthusspp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodesbrassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp.,Aonidiella auranti, Aphididae, Aphis spp., Aspidiotus spp., Aulacorthumsolani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp,Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop.,Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi,Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccushesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri,Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum,Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphispseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopusclypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni,Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp.,Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus,Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp.,Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter,Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigusspp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxeraspp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp.,Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica,Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphumspp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp.,Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina,Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp,Trioza erytreae, Unaspis citri, Zygina flammigera, and Zyginidiascutellaris;

from the order Hymenoptera, for example, Acromyrmex, Arge spp, Attaspp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma,Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp.,Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;from the order Isoptera, for example, Coptotermes spp, Corniternescumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp,Microtermes spp, Reticulitermes spp.; Solenopsis geminate; from theorder Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeriaspp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsiagemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographaspp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella,Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchiatopiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp.,Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambusspp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalimaperspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp.,Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp.,Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp.,Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia,Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis,Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella,Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp.,Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp.,Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctuaspp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammenespp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophoragossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaeaoperculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp.,Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp.,Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate,Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tutaabsoluta, and Yponomeuta spp.;

from the order Mallophaga, for example, Damalinea spp. and Trichodectesspp.;

from the order Orthoptera, for example, Blatta spp., Blattella spp.,Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtillahexadactyla, Periplaneta spp., Scapteriscus spp, and Schistocerca spp.;

from the order Psocoptera, for example, Liposcelis spp.;

from the order Siphonaptera, for example, Ceratophyllus spp.,Ctenocephalides spp. and Xenopsylla cheopis;

from the order Thysanoptera, for example, Calliothrips phaseoli,Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothripsspp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp.,Thrips spp; and/or

from the order Thysanura, for example, Lepisma saccharina.

Examples of soil-inhabiting pests, which can damage a crop in the earlystages of plant development, are:

from the order Lepidoptera, for example, Acleris spp., Aegeria spp.,Agrotis spp., Alabama argillaceae, Amylois spp., Autographa spp.,Busseola fusca, Cadra cautella, Chilo spp., Crocidolomia binotalis,Diatraea spp., Diparopsis castanea, Elasmopalpus spp., Heliothis spp.,Mamestra brassicae, Phthorimaea operculella, Plutella xylostella,Scirpophaga spp., Sesamia spp., Spodoptera spp. and Tortrix spp.;

from the order Coleoptera, for example, Agriotes spp., Anthonomus spp.,Atomaria linearis, Chaetocnema tibialis, Conotrachelus spp.,Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp.,Dilopoderus spp., Epilachna spp., Eremnus spp., Heteronychus spp.,Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchusspp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp.,Scarabeidae, Sitotroga spp., Somaticus spp., Tanymecus spp., Tenebriospp., Tribolium spp., Trogoderma spp. and Zabrus spp.;

from the order Orthoptera, for example, Gryllotalpa spp.;

from the order Isoptera, for example, Reticulitermes spp.;

from the order Psocoptera, for example, Liposcelis spp.;

from the order Anoplura, for example, Haematopinus spp., Linognathusspp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Homoptera, for example, Eriosoma larigerum;

from the order Hymenoptera, for example, Acromyrmex, Atta spp., Cephusspp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsisspp. and Vespa spp.;

from the order Diptera, for example, Tipula spp.;

crucifer flea beetles (Phyllotreta spp.), root maggots (Delia spp.),cabbage seedpod weevil (Ceutorhynchus spp.) and aphids.

The compounds according to any one of embodiments 1 to 22 may be usefulfor the control of nematodes. Thus, in an embodiment 23, the inventionalso relates to a method of controlling damage to plant and partsthereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic-and Ectoparasitic nematodes), especially plant parasitic nematodes suchas root knot nematodes, Meloidogyne hapla, Meloidogyne incognita,Meloidogyne javanica, Meloidogyne arenaria and other Meloidogynespecies; cyst-forming nematodes, Globodera rostochiensis and otherGlobodera species; Heterodera avenae, Heterodera glycines, Heteroderaschachtii, Heterodera trifolii, and other Heterodera species; Seed gallnematodes, Anguina species; Stem and foliar nematodes, Aphelenchoidesspecies; Sting nematodes, Eelonolaimus longicaudatus and otherBelonolaimus species; Pine nematodes, Bursaphelenchus xylophilus andother Bursaphelenchus species; Ring nematodes, Criconema species,Criconemella species, Criconemoides species, Mesocriconema species; Stemand bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci andother Ditylenchus species; Awl nematodes, Dolichodorus species; Spiralnematodes, Heliocotylenchus multicinctus and other Helicotylenchusspecies; Sheath and sheathoid nematodes, Hemicycliophora species andHemicriconemoides species; Hirshmanniella species; Lance nematodes,Hoploaimus species; false rootknot nematodes, Nacobbus species; Needlenematodes, Longidorus elongatus and other Longidorus species; Pinnematodes, Pratylenchus species; Lesion nematodes, Pratylenchusneglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchusgoodeyi and other Pratylenchus species; Burrowing nematodes, Radopholussimilis and other Radopholus species; Reniform nematodes, Rotylenchusrobustus, Rotylenchus reniformis and other Rotylenchus species;Scutellonema species; Stubby root nematodes, Trichodorus primitivus andother Trichodorus species, Paratrichodorus species; Stunt nematodes,Tylenchorhynchus claytoni, Tylenchorhynchus dubius and otherTylenchorhynchus species; Citrus nematodes, Tylenchulus species; Daggernematodes, Xiphinema species; and other plant parasitic nematodespecies, such as Subanguina., spp Hypsoperine spp., Macroposthonia spp.,Melinius spp., Punctodera spp., and Quinisulcius spp. In particular, thenematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. andPratylenchus spp. can be controlled by the compounds according to anyone of embodiment 1 to 22. The active ingredients according to theinvention can be used for controlling, i. e. containing or destroying,pests of the abovementioned type which occur in particular on plants,especially on useful plants and ornamentals in agriculture, inhorticulture and in forests, or on organs, such as fruits, flowers,foliage, stalks, tubers or roots, of such plants, and in some cases evenplant organs which are formed at a later point in time remain protectedagainst these pests.

Suitable target crops are, in particular, cereals, such as wheat,barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodderbeet; fruit, for example pomaceous fruit, stone fruit or soft fruit,such as apples, pears, plums, peaches, almonds, cherries or berries, forexample strawberries, raspberries or blackberries; leguminous crops,such as beans, lentils, peas or soya; oil crops, such as oilseed rape,mustard, poppies, olives, sunflowers, coconut, castor, cocoa or groundnuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants,such as cotton, flax, hemp or jute; citrus fruit, such as oranges,lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce,asparagus, cabbages, carrots, onions, tomatoes, potatoes or bellpeppers; Lauraceae, such as avocado, Cinnamonium or camphor; and alsotobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines,hops, the plantain family, latex plants and ornamentals.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Further areas of use of the compositions according to the invention arethe protection of stored goods and store ambients and the protection ofraw materials, such as wood, textiles, floor coverings or buildings, andalso in the hygiene sector, especially the protection of humans,domestic animals and productive livestock against pests of the mentionedtype.

In an embodiment 24, there is also provided a method for controllingpests (such as mosquitoes and other disease vectors). In embodiment 25,the method for controlling pests comprises applying the compositionsaccording to any one of embodiments 1 to 22 to the pests or theirenvironment, to their locus, for example the soil or to a surface orsubstrate by brushing, rolling, spraying, spreading or dipping. By wayof example, an IRS (indoor residual spraying) application of a surfacesuch as a wall, ceiling or floor surface is contemplated by the methodof the invention. In an embodiment 26, it is contemplated to apply suchcompositions to a substrate such as non-woven or a fabric material inthe form of (or which can be used in the manufacture of) netting,clothing, bedding, curtains and tents.

Substrates including non-woven, fabrics or netting to be treated may bemade of natural fibres such as cotton, raffia, jute, flax, sisal,hessian, or wool, or synthetic fibres such as polyamide, polyester,polypropylene, polyacrylonitrile or the like. The polyesters areparticularly suitable. The methods of textile treatment are known, e.g.WO 2008/151984, WO 2003/034823, U.S. Pat. No. 5,631,072, WO 2005/64072,WO2006/128870, EP 1724392, WO2005113886 or WO 2007/090739.

In embodiment 27, the invention therefore also relates to pesticidalcompositions such as emulsifiable concentrates, suspension concentrates,microemulsions, oil dispersibles, directly sprayable or dilutablesolutions, spreadable pastes, dilute emulsions, soluble powders,dispersible powders, wettable powders, dusts, granules or encapsulationsin polymeric substances, which comprise—at least—one compound accordingto any one of embodiments 1 to 22 and which are to be selected to suitthe intended aims and the prevailing circumstances.

Thus, in embodiment 28, the invention therefore relates to a pesticidalcomposition, which comprises at least one compound according to any oneof embodiments 1 to 22 as active ingredient and at least one auxiliary.

Hence, in embodiment 29, the method for controlling such pests comprisesapplying a pesticidally effective amount of a composition according toembodiment 28 to the target pests, to their locus, or to a surface orsubstrate so as to provide effective residual pesticidal activity on thesurface or substrate. Such application may be made by brushing, rolling,spraying, spreading or dipping the pesticidal composition of theinvention. By way of example, an IRS application of a surface such as awall, ceiling or floor surface is contemplated by the method of theinvention so as to provide effective residual pesticidal activity on thesurface. In another embodiment 30, it is contemplated to apply acomposition according to embodiment 28 for residual control of pests ona substrate such as a fabric material in the form of (or which can beused in the manufacture of) netting, clothing, bedding, curtains andtents.

In these compositions, the active ingredient is employed in pure form, asolid active ingredient for example in a specific particle size, or,preferably, together with—at least—one of the auxiliaries conventionallyused in the art of formulation, such as extenders, for example solventsor solid carriers, or such as surface-active compounds (surfactants).Examples of suitable solvents are: unhydrogenated or partiallyhydrogenated aromatic hydrocarbons, preferably the fractions C₈ to C₁₂of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes ortetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such asparaffins or cyclohexane, alcohols such as ethanol, propanol or butanol,glycols and their ethers and esters such as propylene glycol,dipropylene glycol ether, ethylene glycol or ethylene glycol monomethylether or ethylene glycol monoethyl ether, ketones, such ascyclohexanone, isophorone or diacetone alcohol, strongly polar solvents,such as N-methylpyrrolid-2-one, dimethyl sulfoxide orN,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils,such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil,and silicone oils.

Solid carriers which are used for example for dusts and dispersiblepowders are, as a rule, ground natural minerals such as calcite, talc,kaolin, montmorillonite or attapulgite. To improve the physicalproperties, it is also possible to add highly disperse silicas or highlydisperse absorbtive polymers. Suitable adsorptive carriers for granulesare porous types, such as pumice, brick grit, sepiolite or bentonite,and suitable non-sorptive carrier materials are calcite or sand. Inaddition, a large number of granulated materials of inorganic or organicnature can be used, in particular dolomite or comminuted plant residues.

Suitable surface-active compounds are, depending on the type of theactive ingredient to be formulated, non-ionic, cationic and/or anionicsurfactants or surfactant mixtures which have good emulsifying,dispersing and wetting properties. The surfactants mentioned below areonly to be considered as examples; a large number of further surfactantswhich are conventionally used in the art of formulation and suitableaccording to the invention are described in the relevant literature.

Suitable non-ionic surfactants are, especially, polyglycol etherderivatives of aliphatic or cycloaliphatic alcohols, of saturated orunsaturated fatty acids or of alkyl phenols which may containapproximately 3 to approximately 30 glycol ether groups andapproximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatichydrocarbon radical or approximately 6 to approximately 18 carbon atomsin the alkyl moiety of the alkyl phenols. Also suitable arewater-soluble polyethylene oxide adducts with polypropylene glycol,ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having1 to approximately 10 carbon atoms in the alkyl chain and approximately20 to approximately 250 ethylene glycol ether groups and approximately10 to approximately 100 propylene glycol ether groups. Normally, theabovementioned compounds contain 1 to approximately 5 ethylene glycolunits per propylene glycol unit. Examples which may be mentioned arenonylphenoxypolyethoxyethanol, castor oil polyglycol ether,polypropylene glycol/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol oroctylphenoxypolyethoxyethanol. Also suitable are fatty acid esters ofpolyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, especially, quarternary ammonium saltswhich generally have at least one alkyl radical of approximately 8 toapproximately 22 C atoms as substituents and as further substituents(unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzylradicals. The salts are preferably in the form of halides,methylsulfates or ethylsulfates. Examples are stearyltrimethylammoniumchloride and benzylbis(2-chloroethyl)ethylammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps orwater-soluble synthetic surface-active compounds. Examples of suitablesoaps are the alkali, alkaline earth or (unsubstituted or substituted)ammonium salts of fatty acids having approximately 10 to approximately22 C atoms, such as the sodium or potassium salts of oleic or stearicacid, or of natural fatty acid mixtures which are obtainable for examplefrom coconut or tall oil; mention must also be made of the fatty acidmethyl taurates. However, synthetic surfactants are used morefrequently, in particular fatty sulfonates, fatty sulfates, sulfonatedbenzimidazole derivatives or alkylaryl sulfonates. As a rule, the fattysulfonates and fatty sulfates are present as alkali, alkaline earth or(substituted or unsubstituted) ammonium salts and they generally have analkyl radical of approximately 8 to approximately 22 C atoms, alkyl alsoto be understood as including the alkyl moiety of acyl radicals;examples which may be mentioned are the sodium or calcium salts oflignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcoholsulfate mixture prepared from natural fatty acids. This group alsoincludes the salts of the sulfuric esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonyl groups and a fatty acid radical ofapproximately 8 to approximately 22 C atoms. Examples ofalkylarylsulfonates are the sodium, calcium or triethanolammonium saltsof decylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of anaphthalenesulfonic acid/formaldehyde condensate. Also possible are,furthermore, suitable phosphates, such as salts of the phosphoric esterof a p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.

As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%,of active ingredient and 1 to 99.9%, especially 5 to 99.9%, of at leastone solid or liquid adjuvant, it being possible as a rule for 0 to 25%,especially 0.1 to 20%, of the composition to be surfactants (% in eachcase meaning percent by weight). Whereas concentrated compositions tendto be preferred for commercial goods, the end consumer as a rule usesdilute compositions which have substantially lower concentrations ofactive ingredient.

Typically, a pre-mix formulation for foliar application comprises 0.1 to99.9%, especially 1 to 95%, of the desired ingredients, and 99.9 to0.1%, especially 99 to 5%, of a solid or liquid adjuvant (including, forexample, a solvent such as water), where the auxiliaries can be asurfactant in an amount of 0 to 50%, especially 0.5 to 40%, based on thepre-mix formulation.

Normally, a tank-mix formulation for seed treatment applicationcomprises 0.25 to 80%, especially 1 to 75%, of the desired ingredients,and 99.75 to 20%, especially 99 to 25%, of a solid or liquid auxiliaries(including, for example, a solvent such as water), where the auxiliariescan be a surfactant in an amount of 0 to 40%, especially 0.5 to 30%,based on the tank-mix formulation.

Typically, a pre-mix formulation for seed treatment applicationcomprises 0.5 to 99.9%, especially 1 to 95%, of the desired ingredients,and 99.5 to 0.1%, especially 99 to 5%, of a solid or liquid adjuvant(including, for example, a solvent such as water), where the auxiliariescan be a surfactant in an amount of 0 to 50%, especially 0.5 to 40%,based on the pre-mix formulation.

Whereas commercial products will preferably be formulated asconcentrates (e.g., pre-mix composition (formulation)), the end userwill normally employ dilute formulations (e.g., tank mix composition).

Preferred seed treatment pre-mix formulations are aqueous suspensionconcentrates. The formulation can be applied to the seeds usingconventional treating techniques and machines, such as fluidized bedtechniques, the roller mill method, rotostatic seed treaters, and drumcoaters. Other methods, such as spouted beds may also be useful. Theseeds may be presized before coating. After coating, the seeds aretypically dried and then transferred to a sizing machine for sizing.Such procedures are known in the art. In general, the pre-mixcompositions of the invention contain 0.5 to 99.9 especially 1 to 95,advantageously 1 to 50%, by mass of the desired ingredients, and 99.5 to0.1, especially 99 to 5%, by mass of a solid or liquid adjuvant(including, for example, a solvent such as water), where the auxiliaries(or adjuvant) can be a surfactant in an amount of 0 to 50, especially0.5 to 40%, by mass based on the mass of the pre-mix formulation.

Examples of foliar formulation types for pre-mix compositions are:

GR: Granules

WP: wettable powders

WG: water dispersable granules (powders)

SG: water soluble granules

SL: soluble concentrates

EC: emulsifiable concentrate

EW: emulsions, oil in water

ME: micro-emulsion

SC: aqueous suspension concentrate

CS: aqueous capsule suspension

OD: oil-based suspension concentrate, and

SE: aqueous suspo-emulsion.

Whereas, examples of seed treatment formulation types for pre-mixcompositions are:

WS: wettable powders for seed treatment slurry

LS: solution for seed treatment

ES: emulsions for seed treatment

FS: suspension concentrate for seed treatment

WG: water dispersible granules, and

CS: aqueous capsule suspension.

Examples of formulation types suitable for tank-mix compositions aresolutions, dilute emulsions, suspensions, or a mixture thereof, anddusts.

Preferred compositions are composed in particular as follows (%=percentby weight):

Emulsifiable Concentrates:

active ingredient: 1 to 95%, preferably 5 to 20%

surfactant: 1 to 30%, preferably 10 to 20%

solvent: 5 to 98%, preferably 70 to 85%

Dusts:

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension Concentrates:

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 24%, preferably 88 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable Powders:

active ingredient: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 99%, preferably 15 to 98%

Granulates:

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%

The activity of compositions comprising compounds according to theinvention can be broadened considerably, and adapted to prevailingcircumstances, by including other active substances. The activesubstances can be of chemical or biological in type, and in the case ofbiological could be further modified from the biological species derivedin nature. Active substances include substances that control, repel orattract pests that damage or harm useful plants in general, but alsosubstances that improve the growth of a useful plant, such as plantgrowth regulators, and substances that improve the performance of theactive substance, such as synergists. Examples are insecticides,acaricides, nematicides, molluscicides, aligicides, virusicides,rodenticide, bactericides, fungicides, chemosterilants, anthelmintics.Examples of a biological active substance include baculovirus, plantextract, and bacteria.

The mixtures of the compounds according to any one of embodiments 1 to22 with other active substances may also have further surprisingadvantages which can also be described, in a wider sense, as synergisticactivity. For example, better tolerance by plants, reducedphytotoxicity, insects can be controlled in their different developmentstages, or better behaviour relating to production, for example grindingor mixing, storage or use.

Individual active substances can occur in more than one group or class,and at more than one place within a group or class: information aboutthe active substances, their spectrum, sources and classifications canbe found from Compendium of Pesticide Common Names (seehttp://www.alanwood.net/pesticides/index.html) or from the PesticideManual created by the British Crop Production Counci (seehttp://bcpcdata.com/pesticide-manual.html).

Preferred mixtures are indicated below where a compound according to anyone of embodiment 1 to 22 is indicated as “I”.

Compositions comprising an adjuvant include I+compounds selected fromthe group of substances consisting of petroleum oils;

Compositions comprising an acaricide includeI+1,1-bis(4-chlorophenyl)-2-ethoxyethanol, I+2,4-dichlorophenylbenzenesulfonate, I+2-fluoro-N-methyl-N-1-naphthylacetamide,I+4-chlorophenyl phenyl sulfone, I+abamectin, I+acequinocyl,I+acetoprole, I+acrinathrin, I+aldicarb, I+aldoxycarb,I+alpha-cypermethrin, I+amidithion, I+amidoflumet, I+amidothioate,I+amiton, I+amiton hydrogen oxalate, I+amitraz, I+aramite, I+arsenousoxide, I+AVI 382, I+AZ 60541, I+azinphos-ethyl, I+azinphos-methyl,I+azobenzene, I+azocyclotin, I+azothoate, I+benomyl, I+benoxafos,I+benzoximate, I+benzyl benzoate, I+bifenazate, I+bifenthrin,I+binapacryl, I+brofenvalerate, I+bromocyclen, I+bromophos,I+bromophos-ethyl, I+bromopropylate, I+buprofezin, I+butocarboxim,I+butoxycarboxim, I+butylpyridaben, I+calcium polysulfide,I+camphechlor, I+carbanolate, I+carbaryl, I+carbofuran,I+carbophenothion, I+CGA 50′439, I+chinomethionat, I+chlorbenside,I+chlordimeform, I+chlordimeform hydrochloride, I+chlorfenapyr,I+chlorfenethol, I+chlorfenson, I+chlorfensulfide, I+chlorfenvinphos,I+chlorobenzilate, I+chloromebuform, I+chloromethiuron,I+chloropropylate, I+chlorpyrifos, I+chlorpyrifos-methyl,I+chlorthiophos, I+cinerin I, I+cinerin II, I+cinerins, I+clofentezine,I+closantel, I+coumaphos, I+crotamiton, I+crotoxyphos, I+cufraneb,I+cyanthoate, I+cyflumetofen, I+cyhalothrin, I+cyhexatin,I+cypermethrin, I+DCPM, I+DDT, I+demephion, I+demephion-O,I+demephion-S, I+demeton, I+demeton-methyl, I+demeton-O,I+demeton-O-methyl, I+demeton-S, I+demeton-S-methyl,I+demeton-S-methylsulfon, I+diafenthiuron, I+dialifos, I+diazinon,I+dichlofluanid, I+dichlorvos, I+dicliphos, I+dicofol, I+dicrotophos,I+dienochlor, I+dimefox, I+dimethoate, I+dinactin, I+dinex,I+dinex-diclexine, I+dinobuton, I+dinocap, I+dinocap-4, I+dinocap-6,I+dinocton, I+dinopenton, I+dinosulfon, I+dinoterbon, I+dioxathion,I+diphenyl sulfone, I+disulfiram, I+disulfoton, I+DNOC, I+dofenapyn,I+doramectin, I+endosulfan, I+endothion, I+EPN, I+eprinomectin,I+ethion, I+ethoate-methyl, I+etoxazole, I+etrimfos, I+fenazaflor,I+fenazaquin, I+fenbutatin oxide, I+fenothiocarb, I+fenpropathrin,I+fenpyrad, I+fenpyroximate, I+fenson, I+fentrifanil, I+fenvalerate,I+fipronil, I+fluacrypyrim, I+fluazuron, I+flubenzimine,I+flucycloxuron, I+flucythrinate, I+fluenetil, I+flufenoxuron,I+flumethrin, I+fluorbenside, I+fluvalinate, I+FMC 1137, I+formetanate,I+formetanate hydrochloride, I+formothion, I+formparanate, I+gamma-HCH,I+glyodin, I+halfenprox, I+heptenophos, I+hexadecylcyclopropanecarboxylate, I+hexythiazox, I+iodomethane, I+isocarbophos,I+isopropyl 0-(methoxyaminothiophosphoryl)salicylate, I+ivermectin,I+jasmolin I, I+jasmolin II, I+jodfenphos, I+lindane, I+lufenuron,I+malathion, I+malonoben, I+mecarbam, I+mephosfolan, I+mesulfen,I+methacrifos, I+methamidophos, I+methidathion, I+methiocarb,I+methomyl, I+methyl bromide, I+metolcarb, I+mevinphos, I+mexacarbate,I+milbemectin, I+milbemycin oxime, I+mipafox, I+monocrotophos,I+morphothion, I+moxidectin, I+naled, I+NC-184, I+NC-512, I+nifluridide,I+nikkomycins, I+nitrilacarb, I+nitrilacarb 1:1 zinc chloride complex,I+NNI-0101, I+NNI-0250, I+omethoate, I+oxamyl, I+oxydeprofos,I+oxydisulfoton, I+pp′-DDT, I+parathion, I+permethrin, I+petroleum oils,I+phenkapton, I+phenthoate, I+phorate, I+phosalone, I+phosfolan,I+phosmet, I+phosphamidon, I+phoxim, I+pirimiphos-methyl,I+polychloroterpenes, I+polynactins, I+proclonol, I+profenofos,I+promacyl, I+propargite, I+propetamphos, I+propoxur, I+prothidathion,I+prothoate, I+pyrethrin I, I+pyrethrin II, I+pyrethrins, I+pyridaben,I+pyridaphenthion, I+pyrimidifen, I+pyrimitate, I+quinalphos,I+quintiofos, I+R-1492, I+RA-17, I+rotenone, I+schradan, I+sebufos,I+selamectin, I+SI-0009, I+sophamide, I+spirodiclofen, I+spiromesifen,I+SSI-121, I+sulfiram, I+sulfluramid, I+sulfotep, I+sulfur, I+SZI-121,I+tau-fluvalinate, I+tebufenpyrad, I+TEPP, I+terbam,I+tetrachlorvinphos, I+tetradifon, I+tetranactin, I+tetrasul,I+thiafenox, I+thiocarboxime, I+thiofanox, I+thiometon, I+thioquinox,I+thuringiensin, I+triamiphos, I+triarathene, I+triazophos, I+triazuron,I+trichlorfon, I+trifenofos, I+trinactin, I+vamidothion, I+vaniliproleand I+YI-5302;

Compositions comprising an anthelmintic include I+abamectin,I+crufomate, I+doramectin, I+emamectin, I+emamectin benzoate,I+eprinomectin, I+ivermectin, I+milbemycin oxime, I+moxidectin,I+piperazine, I+selamectin, I+spinosad and I+thiophanate;

Compositions comprising an avicide include I+chloralose, I+endrin,I+fenthion, I+pyridin-4-amine and I+strychnine;

Compositions comprising a biological control agent include I+Adoxophyesorana GV, I+Agrobacterium radiobacter, I+Amblyseius spp., I+Anagraphafalcifera NPV, I+Anagrus atomus, I+Aphelinus abdominalis, I+Aphidiuscolemani, I+Aphidoletes aphidimyza, I+Autographa californica NPV,I+Bacillus firmus, I+Bacillus sphaericus Neide, I+Bacillus thuringiensisBerliner, I+Bacillus thuringiensis subsp. aizawai, I+Bacillusthuringiensis subsp. israelensis, I+Bacillus thuringiensis subsp.japonensis, I+Bacillus thuringiensis subsp. kurstaki, I+Bacillusthuringiensis subsp. tenebrionis, I+Beauveria bassiana, I+Beauveriabrongniartii, I+Chrysoperla carnea, I+Cryptolaemus montrouzieri, I+Cydiapomonella GV, I+Dacnusa sibirica, I+Diglyphus isaea, I+Encarsia formosa,I+Eretmocerus eremicus, I+Helicoverpa zea NPV, I+Heterorhabditisbacteriophora and H. megidis, I+Hippodamia convergens, I+Leptomastixdactylopii, I+Macrolophus caliginosus, I+Mamestra brassicae NPV,I+Metaphycus helvolus, I+Metarhizium anisopliae var. acridum,I+Metarhizium anisopliae var. anisopliae, I+Neodiprion sertifer NPV andN. lecontei NPV, I+Orius spp., I+Paecilomyces fumosoroseus,I+Phytoseiulus persimilis, I+Spodoptera exigua multicapsid nuclearpolyhedrosis virus, I+Steinernema bibionis, I+Steinernema carpocapsae,I+Steinernema feltiae, I+Steinernema glaseri, I+Steinernema riobrave,I+Steinernema riobravis, I+Steinernema scapterisci, I+Steinernema spp.,I+Trichogramma spp., I+Typhlodromus occidentalis and I+Verticilliumlecanii;

Compositions comprising a soil sterilant include I+iodomethane andmethyl bromide; Compositions comprising a chemosterilant includeI+apholate, I+bisazir, I+busulfan, I+diflubenzuron, I+dimatif, I+hemel,I+hempa, I+metepa, I+methiotepa, I+methyl apholate, I+morzid,I+penfluron, I+tepa, I+thiohempa, I+thiotepa, I+tretamine and I+uredepa;Compositions comprising an insect pheromone include I+(E)-dec-5-en-1-ylacetate with (E)-dec-5-en-1-ol, I+(E)-tridec-4-en-1-yl acetate,I+(E)-6-methylhept-2-en-4-ol, I+(E,Z)-tetradeca-4,10-dien-1-yl acetate,I+(Z)-dodec-7-en-1-yl acetate, I+(Z)-hexadec-11-enal,I+(Z)-hexadec-11-en-1-yl acetate, I+(Z)-hexadec-13-en-11-yn-1-ylacetate, I+(Z)-icos-13-en-10-one, I+(Z)-tetradec-7-en-1-al,I+(Z)-tetradec-9-en-1-ol, I+(Z)-tetradec-9-en-1-yl acetate,I+(7E,9Z)-dodeca-7,9-dien-1-yl acetate,I+(9Z,11E)-tetradeca-9,11-dien-1-yl acetate,I+(9Z,12E)-tetradeca-9,12-dien-1-yl acetate, I+14-methyloctadec-1-ene,I+4-methylnonan-5-ol with 4-methylnonan-5-one, I+alpha-multistriatin,I+brevicomin, I+codlelure, I+codlemone, I+cuelure, I+disparlure,I+dodec-8-en-1-yl acetate, I+dodec-9-en-1-yl acetate, I+dodeca-8,I+10-dien-1-yl acetate, I+dominicalure, I+ethyl 4-methyloctanoate,I+eugenol, I+frontalin, I+gossyplure, I+grandlure, I+grandlure I,I+grandlure II, I+grandlure Ill, I+grandlure IV, I+hexalure,I+ipsdienol, I+ipsenol, I+japonilure, I+lineatin, I+litlure, I+looplure,I+medlure, I+megatomoic acid, I+methyl eugenol, I+muscalure,I+octadeca-2,13-dien-1-yl acetate, I+octadeca-3,13-dien-1-yl acetate,I+orfralure, I+oryctalure, I+ostramone, I+siglure, I+sordidin,I+sulcatol, I+tetradec-11-en-1-yl acetate, I+trimedlure, I+trimedlure A,I+trimedlure B₁, I+trimedlure B₂, I+trimedlure C and I+trunc-call;

Compositions comprising an insect repellent includeI+2-(octylthio)ethanol, I+butopyronoxyl, I+butoxy(polypropylene glycol),I+dibutyl adipate, I+dibutyl phthalate, I+dibutyl succinate,I+diethyltoluamide, I+dimethyl carbate, I+dimethyl phthalate, I+ethylhexanediol, I+hexamide, I+methoquin-butyl, I+methylneodecanamide,I+oxamate and I+picaridin;

Compositions comprising an insecticide includeI+1-dichloro-1-nitroethane, I+1,1-dichloro-2,2-bis(4-ethylphenyl)ethane,I+, I+1,2-dichloropropane, I+1,2-dichloropropane with1,3-dichloropropene, I+1-bromo-2-chloroethane,I+2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate,I+2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate,I+2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate,I+2-(2-butoxyethoxy)ethyl thiocyanate,I+2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate,I+2-(4-chloro-3,5-xylyloxy)ethanol, I+2-chlorovinyl diethyl phosphate,I+2-imidazolidone, I+2-isovalerylindan-1,3-dione,I+2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, I+2-thiocyanatoethyllaurate, I+3-bromo-1-chloroprop-1-ene, I+3-methyl-1-phenylpyrazol-5-yldimethyl-carbamate, I+4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, I+5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate,I+abamectin, I+acephate, I+acetamiprid, I+acethion, I+acetoprole,I+acrinathrin, I+acrylonitrile, I+alanycarb, I+aldicarb, I+aldoxycarb,I+aldrin, I+allethrin, I+allosamidin, I+allyxycarb,I+alpha-cypermethrin, I+alpha-ecdysone, I+aluminium phosphide,I+amidithion, I+amidothioate, I+aminocarb, I+amiton, I+amiton hydrogenoxalate, I+amitraz, I+anabasine, I+athidathion, I+AVI 382, I+AZ 60541,I+azadirachtin, I+azamethiphos, I+azinphos-ethyl, I+azinphos-methyl,I+azothoate, I+Bacillus thuringiensis delta endotoxins, I+bariumhexafluorosilicate, I+barium polysulfide, I+barthrin, I+Bayer 22/190,I+Bayer 22408, I+bendiocarb, I+benfuracarb, I+bensultap,I+beta-cyfluthrin, I+beta-cypermethrin, I+bifenthrin, I+bioallethrin,I+bioallethrin S-cyclopentenyl isomer, I+bioethanomethrin,I+biopermethrin, I+bioresmethrin, I+bis(2-chloroethyl) ether,I+bistrifluron, I+borax, I+brofenvalerate, I+bromfenvinfos,I+bromocyclen, I+bromo-DDT, I+bromophos, I+bromophos-ethyl, I+bufencarb,I+buprofezin, I+butacarb, I+butathiofos, I+butocarboxim, I+butonate,I+butoxycarboxim, I+butylpyridaben, I+cadusafos, I+calcium arsenate,I+calcium cyanide, I+calcium polysulfide, I+camphechlor, I+carbanolate,I+carbaryl, I+carbofuran, I+carbon disulfide, I+carbon tetrachloride,I+carbophenothion, I+carbosulfan, I+cartap, I+cartap hydrochloride,I+cevadine, I+chlorbicyclen, I+chlordane, I+chlordecone,I+chlordimeform, I+chlordimeform hydrochloride, I+chlorethoxyfos,I+chlorfenapyr, I+chlorfenvinphos, I+chlorfluazuron, I+chlormephos,I+chloroform, I+chloropicrin, I+chlorphoxim, I+chlorprazophos,I+chlorpyrifos, I+chlorpyrifos-methyl, I+chlorthiophos,I+chromafenozide, I+cinerin I, I+cinerin II, I+cinerins,I+cis-resmethrin, I+cismethrin, I+clocythrin, I+cloethocarb,I+closantel, I+clothianidin, I+copper acetoarsenite, I+copper arsenate,I+copper oleate, I+coumaphos, I+coumithoate, I+crotamiton,I+crotoxyphos, I+crufomate, I+cryolite, I+CS 708, I+cyanofenphos,I+cyanophos, I+cyanthoate, I+cyclethrin, I+cycloprothrin, I+cyfluthrin,I+cyhalothrin, I+cypermethrin, I+cyphenothrin, I+cyromazine,I+cythioate, I+d-limonene, I+d-tetramethrin, I+DAEP, I+dazomet, I+DDT,I+decarbofuran, I+deltamethrin, I+demephion, I+demephion-O,I+demephion-S, I+demeton, I+demeton-methyl, I+demeton-O,I+demeton-O-methyl, I+demeton-S, I+demeton-S-methyl,I+demeton-S-methylsulphon, I+diafenthiuron, I+dialifos, I+diamidafos,I+diazinon, I+dicapthon, I+dichlofenthion, I+dichlorvos, I+dicliphos,I+dicresyl, I+dicrotophos, I+dicyclanil, I+dieldrin, I+diethyl5-methylpyrazol-3-yl phosphate, I+diflubenzuron, I+dilor,I+dimefluthrin, I+dimefox, I+dimetan, I+dimethoate, I+dimethrin,I+dimethylvinphos, I+dimetilan, I+dinex, I+dinex-diclexine, I+dinoprop,I+dinosam, I+dinoseb, I+dinotefuran, I+diofenolan, I+dioxabenzofos,I+dioxacarb, I+dioxathion, I+disulfoton, I+dithicrofos, I+DNOC,I+doramectin, I+DSP, I+ecdysterone, I+EI 1642, I+emamectin, I+emamectinbenzoate, I+EMPC, I+empenthrin, I+endosulfan, I+endothion, I+endrin,I+EPBP, I+EPN, I+epofenonane, I+eprinomectin, I+esfenvalerate,I+etaphos, I+ethiofencarb, I+ethion, I+ethiprole, I+ethoate-methyl,I+ethoprophos, I+ethyl formate, I+ethyl-DDD, I+ethylene dibromide,I+ethylene dichloride, I+ethylene oxide, I+etofenprox, I+etrimfos,I+EXD, I+famphur, I+fenamiphos, I+fenazaflor, I+fenchlorphos,I+fenethacarb, I+fenfluthrin, I+fenitrothion, I+fenobucarb,I+fenoxacrim, I+fenoxycarb, I+fenpirithrin, I+fenpropathrin, I+fenpyrad,I+fensulfothion, I+fenthion, I+fenthion-ethyl, I+fenvalerate,I+fipronil, I+flonicamid, I+flubendiamide, I+flucofuron,I+flucycloxuron, I+flucythrinate, I+fluenetil, I+flufenerim,I+flufenoxuron, I+flufenprox, I+flumethrin, I+fluvalinate, I+FMC 1137,I+fonofos, I+formetanate, I+formetanate hydrochloride, I+formothion,I+formparanate, I+fosmethilan, I+fospirate, I+fosthiazate, I+fosthietan,I+furathiocarb, I+furethrin, I+gamma-cyhalothrin, I+gamma-HCH,I+guazatine, I+guazatine acetates, I+GY-81, I+halfenprox,I+halofenozide, I+HCH, I+HEOD, I+heptachlor, I+heptenophos,I+heterophos, I+hexaflumuron, I+HHDN, I+hydramethylnon, I+hydrogencyanide, I+hydroprene, I+hyquincarb, I+imidacloprid, I+imiprothrin,I+indoxacarb, I+iodomethane, I+IPSP, I+isazofos, I+isobenzan,I+isocarbophos, I+isodrin, I+isofenphos, I+isolane, I+isoprocarb,I+isopropyl O-(methoxy-aminothiophosphoryl)salicylate, I+isoprothiolane,I+isothioate, I+isoxathion, I+ivermectin, I+jasmolin I, I+jasmolin II,I+jodfenphos, I+juvenile hormone I, I+juvenile hormone II, I+juvenilehormone Ill, I+kelevan, I+kinoprene, I+lambda-cyhalothrin, I+leadarsenate, I+lepimectin, I+leptophos, I+lindane, I+lirimfos, I+lufenuron,I+lythidathion, I+m-cumenyl methylcarbamate, I+magnesium phosphide,I+malathion, I+malonoben, I+mazidox, I+mecarbam, I+mecarphon, I+menazon,I+mephosfolan, I+mercurous chloride, I+mesulfenfos, I+metaflumizone,I+metam, I+metam-potassium, I+metam-sodium, I+methacrifos,I+methamidophos, I+methanesulfonyl fluoride, I+methidathion,I+methiocarb, I+methocrotophos, I+methomyl, I+methoprene,I+methoquin-butyl, I+methothrin, I+methoxychlor, I+methoxyfenozide,I+methyl bromide, I+methyl isothiocyanate, I+methylchloroform,I+methylene chloride, I+metofluthrin, I+metolcarb, I+metoxadiazone,I+mevinphos, I+mexacarbate, I+milbemectin, I+milbemycin oxime,I+mipafox, I+mirex, I+monocrotophos, I+morphothion, I+moxidectin,I+naftalofos, I+naled, I+naphthalene, I+NC-170, I+NC-184, I+nicotine,I+nicotine sulfate, I+nifluridide, I+nitenpyram, I+nithiazine,I+nitrilacarb, I+nitrilacarb 1:1 zinc chloride complex, I+NNI-0101,I+NNI-0250, I+nornicotine, I+novaluron, I+noviflumuron,I+O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, I+O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, I+O,O-diethylO-6-methyl-2-propylpyrimidin-4-yl phosphorothioate,I+O,O,O′,O′-tetrapropyl dithiopyrophosphate, I+oleic acid, I+omethoate,I+oxamyl, I+oxydemeton-methyl, I+oxydeprofos, I+oxydisulfoton,I+pp′-DDT, I+para-dichlorobenzene, I+parathion, I+parathion-methyl,I+penfluron, I+pentachlorophenol, I+pentachlorophenyl laurate,I+permethrin, I+petroleum oils, I+PH 60-38, I+phenkapton, I+phenothrin,I+phenthoate, I+phorate+TX, I+phosalone, I+phosfolan, I+phosmet,I+phosnichlor, I+phosphamidon, I+phosphine, I+phoxim, I+phoxim-methyl,I+pirimetaphos, I+pirimicarb, I+pirimiphos-ethyl, I+pirimiphos-methyl,I+polychlorodicyclopentadiene isomers, I+polychloroterpenes, I+potassiumarsenite, I+potassium thiocyanate, I+prallethrin, I+precocene I,I+precocene II, I+precocene Ill, I+primidophos, I+profenofos,I+profluthrin, I+promacyl, I+promecarb, I+propaphos, I+propetamphos,I+propoxur, I+prothidathion, I+prothiofos, I+prothoate, I+protrifenbute,I+pymetrozine, I+pyraclofos, I+pyrazophos, I+pyresmethrin, I+pyrethrinI, I+pyrethrin II, I+pyrethrins, I+pyridaben, I+pyridalyl,I+pyridaphenthion, I+pyrimidifen, I+pyrimitate, I+pyriproxyfen,I+quassia, I+quinalphos, I+quinalphos-methyl, I+quinothion,I+quintiofos, I+R-1492, I+rafoxanide, I+resmethrin, I+rotenone, I+RU15525, I+RU 25475, I+ryania, I+ryanodine, I+sabadilla, I+schradan,I+sebufos, I+selamectin, I+SI-0009, I+SI-0205, I+SI-0404, I+SI-0405,I+silafluofen, I+SN 72129, I+sodium arsenite, I+sodium cyanide, I+sodiumfluoride, I+sodium hexafluorosilicate, I+sodium pentachlorophenoxide,I+sodium selenate, I+sodium thiocyanate, I+sophamide, I+spinosad,I+spiromesifen, I+spirotetrmat, I+sulcofuron, I+sulcofuron-sodium,I+sulfluramid, I+sulfotep, I+sulfuryl fluoride, I+sulprofos, I+tar oils,I+tau-fluvalinate, I+tazimcarb, I+TDE, I+tebufenozide, I+tebufenpyrad,I+tebupirimfos, I+teflubenzuron, I+tefluthrin, I+temephos, I+TEPP,I+terallethrin, I+terbam, I+terbufos, I+tetrachloroethane,I+tetrachlorvinphos, I+tetramethrin, I+theta-cypermethrin,I+thiacloprid, I+thiafenox, I+thiamethoxam, I+thicrofos,I+thiocarboxime, I+thiocyclam, I+thiocyclam hydrogen oxalate,I+thiodicarb, I+thiofanox, I+thiometon, I+thionazin, I+thiosultap,I+thiosultap-sodium, I+thuringiensin, I+tolfenpyrad, I+tralomethrin,I+transfluthrin, I+transpermethrin, I+triamiphos, I+triazamate,I+triazophos, I+triazuron, I+trichlorfon, I+trichlormetaphos-3,I+trichloronat, I+trifenofos, I+triflumuron, I+trimethacarb, I+triprene,I+vamidothion, I+vaniliprole, I+veratridine, I+veratrine, I+XMC,I+xylylcarb, I+YI-5302, I+zeta-cypermethrin, I+zetamethrin, I+zincphosphide, I+zolaprofos and ZXI 8901, I+cyantraniliprole,I+chlorantraniliprole, I+cyenopyrafen, I+cyflumetofen,I+pyrifluquinazon, I+spinetoram, I+spirotetramat, I+sulfoxaflor,I+flufiprole, I+meperfluthrin, I+tetramethylfluthrin, I+triflumezopyrim;Compositions comprising a molluscicide include I+bis(tributyltin) oxide,I+bromoacetamide, I+calcium arsenate, I+cloethocarb, I+copperacetoarsenite, I+copper sulfate, I+fentin, I+ferric phosphate,I+metaldehyde, I+methiocarb, I+niclosamide, I+niclosamide-olamine,I+pentachlorophenol, I+sodium pentachlorophenoxide, I+tazimcarb,I+thiodicarb, I+tributyltin oxide, I+trifenmorph, I+trimethacarb,I+triphenyltin acetate and triphenyltin hydroxide, I+pyriprole;Compositions comprising a nematicide include 1+AKD-3088,I+1,2-dibromo-3-chloropropane, I+1,2-dichloropropane,I+1,2-dichloropropane with 1,3-dichloropropene, I+1,3-dichloropropene,I+3,4-dichlorotetrahydrothiophene 1,1-dioxide,I+3-(4-chlorophenyl)-5-methylrhodanine,I+5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid,I+6-isopentenylaminopurine, I+abamectin, I+acetoprole, I+alanycarb,I+aldicarb, I+aldoxycarb, I+AZ 60541, I+benclothiaz, I+benomyl,I+butylpyridaben, I+cadusafos, I+carbofuran, I+carbon disulfide,I+carbosulfan, I+chloropicrin, I+chlorpyrifos, I+cloethocarb,I+cytokinins, I+dazomet, I+DBCP, I+DCIP, I+diamidafos, I+dichlofenthion,I+dicliphos, I+dimethoate, I+doramectin, I+emamectin, I+emamectinbenzoate, I+eprinomectin, I+ethoprophos, I+ethylene dibromide,I+fenamiphos, I+fenpyrad, I+fensulfothion, I+fosthiazate, I+fosthietan,I+furfural, I+GY-81, I+heterophos, I+iodomethane, I+isamidofos,I+isazofos, I+ivermectin, I+kinetin, I+mecarphon, I+metam,I+metam-potassium, I+metam-sodium, I+methyl bromide, I+methylisothiocyanate, I+milbemycin oxime, I+moxidectin, I+Myrotheciumverrucaria composition, I+NC-184, I+oxamyl, I+phorate, I+phosphamidon,I+phosphocarb, I+sebufos, I+selamectin, I+spinosad, I+terbam,I+terbufos, I+tetrachlorothiophene, I+thiafenox, I+thionazin,I+triazophos, I+triazuron, I+xylenols, I+YI-5302 and zeatin,I+fluensulfone;

Compositions comprising a synergist include I+2-(2-butoxyethoxy)ethylpiperonylate, I+5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone,I+farnesol with nerolidol, I+MB-599, I+MGK 264, I+piperonyl butoxide,I+piprotal, I+propyl isomer, I+S421, I+sesamex, I+sesasmolin andI+sulfoxide;

Compositions comprising an animal repellent include 1+anthraquinone,I+chloralose, I+copper naphthenate, I+copper oxychloride, I+diazinon,I+dicyclopentadiene, I+guazatine, I+guazatine acetates, I+methiocarb,I+pyridin-4-amine, I+thiram, I+trimethacarb, I+zinc naphthenate andI+ziram; Further compositions include I+Brofluthrinate, I+Cycloxaprid,I+Diflovidazine, I+Flometoquin, I+Fluhexafon, I+Guadipyr, I+Plutellaxylostella Granulosis virus, I+Cydia pomonella Granulosis virus,I+Harpin, I+Imicyafos, I+Heliothis virescens Nucleopolyhedrovirus,I+Heliothis punctigera Nucleopolyhedrovirus, I+Helicoverpa armigeraNucleopolyhedrovirus, I+Helicoverpa zea Nucleopolyhedrovirus,I+Spodoptera frugiperda Nucleopolyhedrovirus, I+Plutella xylostellaNucleopolyhedrovirus, I+Pasteuria nishizawae, I+p-cymene, I+Pyflubumide,I+Pyrafluprole, I+pyrethrum, I+QRD 420, I+QRD 452, I+QRD 460,I+Terpenoid blends, I+Terpenoids, I+Tetraniliprole, and I+α-terpinene;

Composition also include mixtures of compound of formula I and an activesubstance referenced by a code, such as I+code AE 1887196 (BSC-BX60309),I+code NNI-0745 GR, I+code IKI-3106, I+code JT-L001, I+code ZNQ-08056,I+code IPPA152201, I+code HNPC-A9908 (CAS: [660411-21-2]), I+codeHNPC-A2005 (CAS: [860028-12-2]), I+code JS118, I+code ZJ0967, I+codeZJ2242, I+code JS7119 (CAS: [929545-74-4]), I+code SN-1172, I+codeHNPC-A9835, I+code HNPC-A9955, I+code HNPC-A3061, I+code Chuanhua 89-1,I+code IPP-10, I+code ZJ3265, I+code JS9117, I+code SYP-9080, I+codeZJ3757, I+code ZJ4042, I+code ZJ4014, I+code ITM-121, I+code DPX-RAB55(DKI-2301), I+code Me5382, I+code NC-515, I+code NA-89, I+code MIE-1209,I+code MCI-8007, I+code BCS-CL73507, I+code S-1871, I+code DPX-RDS63,and I+code AKD-1193.

The active ingredient mixture of the compounds according to any one ofembodiments 1 to 22 with active ingredients described above comprises acompound according to any one of embodiments 1 to 22 and an activeingredient as described above preferably in a mixing ratio of from 100:1to 1:6000, especially from 50:1 to 1:50, more especially in a ratio offrom 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are by weight.

In embodiment 31, the mixtures as described above can be used in amethod for controlling pests, which comprises applying a compositioncomprising a mixture as described above to the pests or theirenvironment, with the exception of a method for treatment of the humanor animal body by surgery or therapy and diagnostic methods practised onthe human or animal body.

The mixtures comprising a compound according to any one of embodiments 1to 22 and one or more active ingredients as described above can beapplied, for example, in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds according to any one ofembodiments 1 to 22 and the active ingredients as described above is notessential for working the present invention.

The compositions according to embodiment 31 can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.

The compositions according to embodiment 31 are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.

The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is generally 1 to 2000 g of active ingredient per hectare, inparticular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection isapplication to the foliage of the plants (foliar application), it beingpossible to select frequency and rate of application to match the dangerof infestation with the pest in question. Alternatively, the activeingredient can reach the plants via the root system (systemic action),by drenching the locus of the plants with a liquid composition or byincorporating the active ingredient in solid form into the locus of theplants, for example into the soil, for example in the form of granules(soil application). In the case of paddy rice crops, such granules canbe metered into the flooded paddy-field.

The compounds according to any one of embodiments 1 to 22 andcompositions thereof are also be suitable for the protection of plantpropagation material, for example seeds, such as fruit, tubers orkernels, or nursery plants, against pests of the abovementioned type.The propagation material can be treated with the compound prior toplanting, for example seed can be treated prior to sowing.Alternatively, the compound can be applied to seed kernels (coating),either by soaking the kernels in a liquid composition or by applying alayer of a solid composition. It is also possible to apply thecompositions when the propagation material is planted to the site ofapplication, for example into the seed furrow during drilling. Thesetreatment methods for plant propagation material and the plantpropagation material thus treated are further subjects of the invention.Typical treatment rates would depend on the plant and pest/fungi to becontrolled and are generally between 1 to 200 grams per 100 kg of seeds,preferably between 5 to 150 grams per 100 kg of seeds, such as between10 to 100 grams per 100 kg of seeds.

In embodiment 32, the invention therefore relates to a method for theprotection of plant propagation material from the attack by pests, whichcomprises treating the propagation material or the site, where thepropagation material is planted, with a compound according to any one ofembodiments 1 to 22 or with a composition according to embodiment 28 or31, which comprises at least one compound according to any one ofembodiments 1 to 22, as active ingredient and at least one auxiliarycomposition.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corns, bulbs,fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like andmeans in a preferred embodiment true seeds.

The present invention also comprises seeds coated or treated with orcontaining a compound of formula I. The term “coated or treated withand/or containing” generally signifies that the active ingredient is forthe most part on the surface of the seed at the time of application,although a greater or lesser part of the ingredient may penetrate intothe seed material, depending on the method of application. When the saidseed product is (re)planted, it may absorb the active ingredient. In anembodiment, the present invention makes available a plant propagationmaterial adhered thereto with a compound of formula (I). Further, it ishereby made available, a composition comprising a plant propagationmaterial treated with a compound according to any one of embodiments 1to 22.

Seed treatment comprises all suitable seed treatment techniques known inthe art, such as seed dressing, seed coating, seed dusting, seed soakingand seed pelleting. The seed treatment application of the compoundaccording to any one of embodiments 1 to 22 can be carried out by anyknown methods, such as spraying or by dusting the seeds before sowing orduring the sowing/planting of the seeds.

EXPERIMENTAL

Preparatory Examples: The following examples are intended to illustratethe invention and are not to be construed as being limitations thereon.

“Mp” means melting point in ° C. ¹H NMR measurements were recorded on aBrucker 400 MHz spectrometer, chemical shifts are given in ppm relevantto a TMS standard. Spectra measured in deuterated solvents as indicated.

Example 1: Preparation of[1-(2,6-dimethylphenyl)-3-[[4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino]urea

Step A-1: Preparation of4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzonitrile

To a solution of 5-(trifluoromethoxy)indan-1-one oxime (1.0 eq., 2.07 g)in N,N-dimethylformamide (295 mL), 4-fluorobenzonitrile (1.0 eq., 1.08g) and potassium tert-butoxyde (1.2 eq., 10.7 mL of 1M solution intetrahydrofuran) were added dropwise under argon at 0° C. The mixturewas then allowed to warm to room temperature. After 1 h, the reactionmixture was slowly poured into a mixture of HCl (1M)/ethyl acetate. Theorganic layer was washed with water, brine, dried over Na₂SO₄, filtratedand evaporated. The residue was submitted to column chromatography togive the title compound as a solid.

¹H NMR (400 MHz, CDCl₃) δ ppm: 7.86 (d, 1H), 7.56-7.71 (m, 2H),7.31-7.44 (m, 2H), 7.12-7.26 (m, 2H), 3.18 (s, 4H)

Step A-2: Preparation of4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzaldehyde

To a solution of4-[([6-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzonitrile (1.0 eq.,1.968 g) in dichloromethane (59 mL) was added DIBAL-H (1.0 mol/L) indichloromethane (1.1 eq., 6.5 mL, 8.0 g) at 0° C. The mixture wasstirred at this temperature for 1 h, then quenched by careful additionof water at 0° C. and allowed to warm to room temperature. The aqueouslayer was extracted twice with ethyl acetate, the organic phase driedover sodium sulphate and the solvent evaporated. The crude reactionmixture was used without purification in the following step.

Step A-3: Preparation of[1-(2,6-dimethylphenyl)-3-[[4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino]urea

To a solution of4-[[5-(trifluoromethoxy)indan-1-ylidene]amino]oxybenzaldehyde (1.0 eq.,0.1 g) in methanol (2.9 mL) was added 1-amino-3-(2,6-dimethylphenyl)urea(1.05 eq., 0.056 g) at room temperature. The reaction mixture was thenstirred at 65° C. overnight. The resulting white precipitate wasfiltered, washed twice with methanol and pentane.

Mp=174-176° C. ¹H NMR (400 MHz, DMSO-d₆) δ ppm: 10.44-10.50 (m, 1H),8.44-8.51 (m, 1H), 7.87-7.92 (m, 2H), 7.80-7.86 (m, 2H), 7.47-7.52 (m,1H), 7.32-7.38 (m, 1H), 7.24-7.31 (m, 2H), 7.09 (s, 3H), 3.10-3.21 (m,4H), 2.21 (s, 6H)

Example 2: Preparation of[([4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxyphenyl]methyleneamino]N-(2,6-dimethylphenyl)carbamate

Step B-1: Preparation of4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzonitrile

4-nitrobenzonitrile (1.0 eq., 0.48 g) was added to a mixture of1-[4-(trifluoromethoxy)phenyl]ethanone oxime (1.0 eq., 0.72 g) anddipotassium carbonate (1.0 eq., 0.45 g) in acetonitrile (16 mL). Thereaction mixture was heated at 85° C. and stirred at this temperatureuntil full conversion was observed. The mixture was then allowed to cooldown to room temperature before filtering the precipitate. The solid waswashed with diethyl ether and then was submitted to columnchromatography to give the title compound as a solid.

¹H NMR (400 MHz, CDCl₃) δ ppm: 7.82 (d, 2H), 7.65 (d, 2H), 7.37 (d, 2H),7.30 (d, 2H), 2.49 (s, 3H).

Step B-2: Preparation of4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde

To a solution of4-[1-[3-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzonitrile (1.0eq., 0.64 g) in dichloromethane (20 mL) was added DIBAL-H (1.0 mol/L) indichloromethane (1.1 eq., 2.2 mL) at 0° C.

The mixture was stirred at this temperature for 1 h, then quenched bycareful addition of water at 0° C. and allowed to warm to roomtemperature. The aqueous layer was extracted twice with ethyl acetate,the organic phase dried over sodium sulphate and the solvent evaporated.The crude reaction mixture was used without purification in thefollowing step.

Step B-3: Preparation of[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde oxime

To a solution of4-[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde (1.0eq., 0.06 g) in methanol (0.9 mL) were added hydroxylammonium chloride(2.3 eq., 0.02 mL) then sodium acetate trihydrate (2.5 eq., 0.04 g). Thereaction mixture was then heated at 70° C. and stirred for 1 h. Themixture was then allowed to cool down to room temperature beforefiltering the precipitate. The liquid was evaporated and then dissolvedin a mixture of ethyl acetate/HCl (1N). The aqueous layer was extractedtwice with ethyl acetate, the organic phase dried over sodium sulphateand the solvent evaporated, to afford the title compound as a solid.

¹H NMR (400 MHz, DMSO-d₆) δ ppm: 8.11 (s, 1H), 7.97 (d, 2H), 7.60 (d,2H), 7.48 (d, 2H), 7.31 (d, 2H), 2.47 (s, 3H).

Step B-4: Preparation of[1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxyphenyl]methyleneamino]N-(2,6-dimethylphenyl)carbamate(compound 2)

To a solution of1-[4-(trifluoromethoxy)phenyl]ethylideneamino]oxybenzaldehyde oxime (1.0eq., 59 mg) in tetrahydrofuran (5.5 mL) was added2,6-dimethylphenyl-isocyanate (3.0 eq., 79 mg) under argon at roomtemperature. The reaction mixture was then stirred at 65° C. overnight.The resulting white precipitate was filtered, and then was submitted tocolumn chromatography to give the title compound as a solid. Mp=145-152°C.

1H NMR (400 MHz, CDCl3) δ ppm: 8.41-8.48 (m, 1H), 7.83-7.89 (m, 2H),7.66-7.76 (m, 3H), 7.37-7.43 (m, 2H), 7.31-7.34 (m, 2H), 7.12-7.19 (m,3H), 2.47-2.54 (m, 3H), 2.33-2.40 (m, 6H).

Example 3: Preparation of1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]thiourea

Step C-1: Preparation of tert-butylN-(4-methanehydrazonoylphenyl)carbamate

tert-butyl N-(4-formylphenyl)carbamate (1.0 eq., 0.75 g) was added to asolution of hydrazine hydrate (10.0 eq., 4.8 g) in ethanol (34 mL) at80° C. The resulting mixture was stirred at reflux for 1 h, the allowedto cool down to room temperature. The organic phase dried over sodiumsulphate and the solvent evaporated. The crude reaction mixture was usedwithout purification in the following step.

Step C-2: Preparation of tert-butylN-[4-[[(2,6-dimethylphenyl)carbamothioylhydrazono]methyl]phenyl]carbamate

To a solution of 2-isothiocyanato-1,3-dimethyl-benzene (2.8 eq., 1.3 g)in tetrahydrofuran (29 mL) was added tert-butylN-(4-methanehydrazonoylphenyl)carbamate (1.0 eq., 0.7 g). The reactionmixture was then stirred at 65° C. overnight. The resulting whiteprecipitate was filtered off, the filtrate was evaporated and was thensubmitted to column chromatography to give the title compound as asolid.

1H NMR (400 MHz, DMSO-d6) δ ppm: 11.65 (s, 1H), 9.77 (s, 1H), 9.54 (s,1H), 8.04 (s, 1H), 7.78 (d, 2H), 7.49 (d, 2H), 7.11 (m, 3H), 2.18 (s,6H), 1.48 (s, 9H).

Step C-3: Preparation of1-[(4-aminophenyl)methyleneamino]-3-(2,6-dimethylphenyl)thiourea

To a cold solution of tert-butylN-[4-[[(2,6-dimethylphenyl)carbamothioylhydrazono]methyl]phenyl]carbamate(1.0 eq., 0.55 g) in dichloromethane (7 mL) was added2,2,2-trifluoroacetic acid (5.0 eq., 0.79 g) at room temperature. Thereaction mixture was then stirred overnight at the same temperature. Thesolvent was evaporated and the resulting mixture was poured into ethylacetate/water. Sodium hydroxide (1M) was added to the aqueous layeruntil pH was basic. The aqueous layer was extracted twice with ethylacetate, the organic phase dried over sodium sulphate and the solventevaporated. The crude reaction mixture was purified by flashchromatography, to afford the title compound as a solid.

1H NMR (400 MHz, DMSO-d6) δ ppm: 11.41 (s, 1H), 9.60 (s, 1H), 7.94 (s,1H), 7.53 (d, 2H), 7.09 (m, 3H), 6.54 (d, 2H), 5.60 (s, 2H), 2.18 (s,6H).

Step C-4: Preparation of1-(2,6-dimethylphenyl)-3-[(4-hydrazinophenyl)methyleneamino]thiourea

To solution of1-[4-aminophenyl)methyleneamino]-3-(2,6-dimethylphenyl)thiourea (1.0eq., 0.25 g) in concentrated hydrogen chloride (3.1 mL) at −10° C. wasadded dropwise a solution of sodium nitrite (1.3 aq., 0.07 g) in water(0.3 mL), carefully monitoring that the temperature didn't exceed 5° C.The reaction mixture was stirred for 1 h at 0° C., then cooled down to−40° C. A solution of dichlorotin dihydrate (2.6 eq., 0.49 g) inconcentrated hydrogen chloride (0.5 mL) was added dropwise to thereaction mixture, which was then stirred 1 h at 0° C. The mixture waspoured into dichloromethane/sodium hydroxide (2M), then sodium hydroxidewas added until basic pH. The aqueous layer was extracted twice withethyl acetate, the organic phase dried over sodium sulphate and thesolvent evaporated. The crude reaction mixture was used withoutpurification in the following step.

Step C-5: Preparation of1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]thiourea(compound 3)

To a solution of1-(2,6-dimethylphenyl)-3-[(4-hydrazinophenyl)methyleneamino]thiourea(1.0 eq., 90 mg) in tetrahydrofuran (2.9 mL) was added1-[4-(trifluoromethoxy)phenyl]ethanone (1.0 eq., 58 mg) at roomtemperature. The reaction mixture was then stirred at room temperatureovernight. The mixture was poured into dichloromethane/water, theaqueous layer was extracted twice with dichloromethane, the organicphase dried over sodium sulphate and the solvent evaporated. The crudewas submitted to column chromatography to give the title compound as anamorphous solid.

1H NMR (400 MHz, DMSO-d6) δ ppm: 11.52-11.58 (m, 1H), 9.69-9.73 (m, 1H),9.62-9.68 (m, 1H), 8.03-8.05 (m, 1H), 7.87-7.94 (m, 2H), 7.72-7.80 (m,2H), 7.35-7.42 (m, 2H), 7.22-7.29 (m, 2H), 7.08-7.13 (m, 3H), 2.25-2.31(m, 3H), 2.16-2.20 (m, 6H).

Lc MS Method A: Standard:

Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQSingle quadrupole mass spectrometer) equipped with an electrospraysource (Polarity: positive or negative ions, Capillary: 3.00 kV, Conerange: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C.,Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation GasFlow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC fromWaters: Binary pump, heated column compartment and diode-array detector.Solvent degasser, binary pump, heated column compartment and diode-arraydetector. Column: Waters UPLC HSS T3, 1.8 Waters UPLC HSS, Temp: 60° C.,DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5%MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85.

LC MS Method B: Standard Long:

Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQSingle quadrupole mass spectrometer) equipped with an electrospraysource (Polarity: positive or negative ions, Capillary: 3.00 kV, Conerange: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C.,Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation GasFlow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC fromWaters: Binary pump, heated column compartment and diode-array detector.Solvent degasser, binary pump, heated column compartment and diode-arraydetector. Column: Waters UPLC HSS T3, 1.8 Temp: 60° C., DAD Wavelengthrange (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH,B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 0% B, 100% A;2.7-3.0 min 100% B; Flow (ml/min) 0.85.

LC MS Method C: Unpolar:

Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQSingle quadrupole mass spectrometer) equipped with an electrospraysource (Polarity: positive or negative ions, Capillary: 3.00 kV, Conerange: 30-60 V, Extractor: 2.00 V, Source Temperature: 150° C.,Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr, Desolvation GasFlow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC fromWaters: Binary pump, heated column compartment and diode-array detector.Solvent degasser, binary pump, heated column compartment and diode-arraydetector. Column: Waters UPLC HSS T3, 1.8, Temp: 60° C., DAD Wavelengthrange (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH,B=Acetonitrile+0.05% HCOOH: gradient: gradient: 0 min 40% B, 60% A;1.2-1.5 min 100% B; Flow (ml/min) 0.85.

TABLE Z Examples of compounds according to any one of embodiments 1 to22 Ex- Melting ample Point LC MS/ LC MS No. Structures [° C.] NMR Method 1

174-176 497 (M + H)⁺ R_(t) = 1.25 min A  2

145-152 486 (M + H)⁺ R_(t) = 1.27 min A  3

— 500 (M + H)⁺ R_(t) = 1.22 min A  4

170-172 511 (M + H)⁺ R_(t) = 1.32 min A  5

164-166 527 (M + H)⁺ R_(t) = 1.32 min A  6

148-152 499 (M + H)⁺ R_(t) = 1.30 min A  7

165-167 485 (M + H)⁺ R_(t) = 1.23 min A  8

163-165 515 (M + H)⁺ R_(t) = 1.31 min A  9

172-180 513 (M + H)⁺ R_(t) = 1.28 min A 10

181-183 501 (M + H)⁺ R_(t) = 1.27 min A 11

— 512 (M + H)⁺ R_(t) = 1.23 min A 12

— 468 (M + H)⁺ R_(t) = 1.21 min A 13

— 498 (M + H)⁺ R_(t) = 1.29 min A 14

— 514 (M + H)⁺ R_(t) = 1.31 min A 15

215-223 484 (M + H)⁺ R_(t) = 1.18 min A 16

215-223 500 (M + H)⁺ R_(t) = 1.22 min A 17

— 498 (M + H)⁺ R_(t) = 1.23 min A 18

— 500 (M + H)⁺ R_(t) = 1.20 min A 19

228-240 482 (M + H)⁺ R_(t) = 1.23 min A 20

198-209 498 (M + H)⁺ R_(t) = 1.25 min A 21

215-225 468 (M + H)⁺ R_(t) = 1.17 min A 22

232-240 484 (M + H)⁺ R_(t) = 1.21 min A 23

184-189 514 (M + H)⁺ R_(t) = 1.29 min A 24

215-224 484 (M + H)⁺ R_(t) = 1.16 min A 25

210-222 496 (M + H)⁺ R_(t) = 1.27 min A 26

205-210 512 (M + H)⁺ R_(t) = 1.28 min A 27

212-226 482 (M + H)⁺ R_(t) = 1.20 min A 28

— 498 (M + H)⁺ R_(t) = 1.24 min A 29

— 466 (M + H)⁺ R_(t) = 1.10 min A 30

156-165 553 (M + H)⁺ R_(t) = 1.31 min A 31

166-170 541 (M + H)⁺ R_(t) = 1.29 min A

Biological Examples (%=Percent by Weight, Unless Otherwise Specified)Example B1: Spodoptera littoralis (Egyptian Cotton Leaf Worm)

Cotton leaf discs were placed on agar in 24-well microtiter plates andsprayed with aqueous test solutions prepared from 10,000 ppm DMSO stocksolutions. After drying, the leaf discs were infested with five L1larvae. The samples were assessed for mortality, anti-feedant effect,and growth inhibition in comparison to untreated samples 3 days afterinfestation. Control of Spodoptera littoralis by a test sample is whenat least one of mortality, anti-feedant effect, and growth inhibition ishigher than the untreated sample.

The following compounds resulted in at least 80% control at anapplication rate of 200 ppm: 1, 2, 3, 4, 5, 7, 9, 10, 11, 20, 21, 22,26, 27, 28 and 29.

Example B2: Plutella xylostella (Diamond Back Moth)

24-well microtiter plates with artificial diet were treated with aqueoustest solutions prepared from 10,000 ppm DMSO stock solutions bypipetting. After drying, the plates were infested with L2 larvae (10 to15 per well). The samples were assessed for mortality and growthinhibition in comparison to untreated samples 5 days after infestation.

The following compounds gave an effect of at least 80% in at least oneof the two categories (mortality or growth inhibition) at an applicationrate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 14, 15, 16, 18, 19,20, 21, 22, 23, 25, 26, 27, 28 and 29.

Example B3: Diabrotica balteata (Corn Root Worm)

Maize sprouts, placed on an agar layer in 24-well microtiter plates weretreated with aqueous test solutions prepared from 10,000 ppm DMSO stocksolutions by spraying. After drying, the plates were infested with L2larvae (6 to 10 per well). The samples were assessed for mortality andgrowth inhibition in comparison to untreated samples 4 days afterinfestation.

The following compounds gave an effect of at least 80% in at least oneof the two categories (mortality or growth inhibition) at an applicationrate of 200 ppm: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 19,20, 21, 22, 25, 26, 27, 28, 30 and 31.

The invention claimed is:
 1. A compound of formula (I)

wherein Ar¹ is phenyl which is unsubstituted or substituted by one tothree substituents independently selected from C₁-C₆alkyl,C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₃-C₆halocycloalkyl,C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy, halogen, C₁-C₆alkoxyand C₁-C₆haloalkoxy; Ar² is phenyl which is unsubstituted or substitutedby one to three substituents independently selected from C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl,C₃-C₆halocycloalkyl, C₁-C₃haloalkyl-C₃-C₆cycloalkyl, C₃-C₆cycloalkoxy,halogen, cyano, C₁-C₆alkoxy, C₁-C₆haloalkoxy and —S—C₁-C₆alkyl; X¹ is Oor NR⁶; X² is a bond, —CH₂— or —CH₂CH₂—; W is O or NR²; Y is oxygen orsulfur; R¹ is hydrogen or C₁-C₆alkyl; R² is selected from hydrogen,C₁-C₆alkyl and C₁-C₆haloalkyl; R³ is selected from hydrogen, C₁-C₆alkyland C₁-C₆haloalkyl; R⁶ is hydrogen or C₁-C₆alkyl; J is a group selectedfrom J^(1′), J^(2′), J^(3′), J⁹ and J¹¹:

wherein n is 0, 1 or 2, and R²⁰ is independently selected from hydrogen,C₃-C₆halocycloalkyl and C₁-C₆haloalkoxy; R^(Y) is C₁-C₆alkyl; or J andR^(Y) together with the carbon atom to which they are attached form abicyclic ring of formula

q is 1 or 2; R¹⁶ and R¹⁷ are independently selected from hydrogen,C₃-C₆halocycloalkyl and C₁-C₆haloalkoxy; or an agrochemically acceptablesalt, stereoisomer, tautomer, N-oxide thereof.
 2. A compound accordingto claim 1, of formula (Ia)

or formula (Ib)

wherein R^(a), R^(b) and R^(c) are independently selected from hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy; X¹is O or NR⁶; X² is a bond, —CH₂—or —CH₂CH₂—; W is O or NR²; Y is oxygenor sulfur; R¹ is hydrogen or methyl; R² is hydrogen or C₁-C₆alkyl; R⁶ ishydrogen or C₁-C₆alkyl; R¹⁶ is C₁-C₆haloalkoxy; or an agrochemicallyacceptable salt, stereoisomer, tautomer, N-oxide thereof.
 3. A compoundaccording to claim l, of formula (Ia)

wherein R^(a) is R^(b) and R^(c) are independently selected fromhydrogen, methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxyand —OCF₃; X¹ is selected from O, NH and NCH₃; X² is a bond; W isselected from O, NH and NCH₃; Y is oxygen or sulfur; R¹ is hydrogen ormethyl; R¹⁶ is —OCF₃ or —OCF₂CF₃; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxide thereof.
 4. A compound according toclaim 1, of formula (Ib)

wherein R^(a), R^(b) and R^(c) are independently selected from hydrogen,C₁-C₆alkyl, C₁-C₆haloalkyl, halogen, C₁-C₆alkoxy and C₁-C₆haloalkoxy; X¹is O or NR⁶; X² is a bond, —CH₂— or —CH₂CH₂—; W is O or NR²; Y is oxygenor sulfur; R¹ is hydrogen or methyl; R² is hydrogen or C₁-C₆alkyl; R⁶ ishydrogen or C₁-C₆alkyl; R¹⁶ is C ₁ -C₆haloalkoxy; or an agrochemicallyacceptable salt, stereoisomer, tautomer, N-oxide thereof.
 5. A compoundaccording to claim 1, of formula (Ib)

wherein R^(a) is R^(b) and R^(c) are independently selected fromhydrogen, methyl, isopropyl, trifluoromethyl, chloro, fluoro, methoxyand —OCF₃; X¹ is selected from O, NH and NCH₃; X² is a bond; W isselected from O, NH and NCH₃; Y is oxygen or sulfur; R¹ is hydrogen ormethyl; R¹⁶ is —OCF₃ or —OCF₂CF₃; or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxide thereof.
 6. A compound selected fromExample No. Structures IUPAC Name 1

1-(2,6-dimethylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino] urea 2

[[4-[1-[4-(trifluoromethoxy) phenyl]ethylideneamino]oxyphenyl]methyleneamino]N-(2,6- dimethylphenyl)carbamate 3

1-(2,6-dimethylphenyl)-3- [[4-[2-[1-[4-(trifluoromethoxy)phenyl]ethylidene]hydrazino] phenyl]methyleneamino]thiourea 4

1-(2-isopropylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino] urea 5

1-(2-isopropylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino] thiourea 6

1-(2-isopropylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methyleneamino] urea 7

1-(2,6-dimethylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methyleneamino] urea 8

1-(2-isopropylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methyleneamino] thiourea 9

1-(2,6-dimethylphenyl)-3-[[4-[[5- (trifluoromethoxy)indan-1-ylidene]amino]oxyphenyl]methyleneamino] thiourea 10

1-(2,6-dimethylphenyl)-3-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylideneamino]oxy phenyl]methyleneamino]thiourea 11

1-(2,6-dimethylphenyl)-3-[[4-[2-[5- (trifluoromethoxy)indan-1-ylidene]hydrazino]phenyl]methyleneamino] thiourea 12

[[4-[2-[1-[4-(trifluoromethyl) phenyl]ethylidene]hydrazino]phenyl]methyleneamino] N-(2,6- dimethylphenyl)carbamate 13

1-(2-isopropylphenyl)-3-[[4-[2-[1-[3-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]urea 14

1-(2-isopropylphenyl)-3-[[4-[2-[1-[3-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 15

1-(2,6-dimethylphenyl)-3-[[4-[2-[1- [3-(trifluoromethoxy)phenyl]ethylidene]hydrazino]phenyl] methyleneamino]urea 16

1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[3-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 17

1-(2-isopropylphenyl)-3-[[4-[2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]urea 18

1-(2,6-dimethylphenyl)-3-[[4-[2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 19

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]urea 20

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 21

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]urea 22

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]ethylidene] hydrazino]phenyl]methyleneamino]thiourea 23

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]thiourea 24

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[2-(trifluoromethoxy)phenyl]ethylidene] hydrazino]phenyl]methylene-amino]urea 25

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]urea 26

1-(2-isopropylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]thiourea 27

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]urea 28

1-(2,6-dimethylphenyl)-3-[(E)-[4- [(2E)-2-[1-[4-(trifluoromethyl)phenyl]propylidene] hydrazino]phenyl]methyleneamino]thiourea 29

1-[[4-[2-[1-[4- (difluoromethoxy)phenyl]ethylidene]hydrazino]phenyl]methyleneamino]- 3-(2,6-dimethylphenyl)urea 30

1-[[4-[[5-(trifluoromethoxy)indan-1- ylidene]amino]oxyphenyl]methylene-amino]-3-[2- (trifluoromethyl)phenyl]thiourea 31

1-[[4-[1-[4- (trifluoromethoxy)phenyl]ethylidene-amino]oxyphenyl]methylene- amino]-3-[2- (trifluoromethyl)phenyl]thiourea

or an agrochemically acceptable salt, stereoisomer, tautomer, N-oxidethereof.
 7. A pesticidal composition, which comprises at least onecompound according to claim 1, or an agrochemically acceptable salt,stereoisomer, tautomer, N-oxide thereof, as active ingredient and atleast one auxiliary.
 8. The composition according to claim 7, whichfurther comprises one or more other insecticidally, acaricidally,nematicidally and/or fungicidally active agents.
 9. A method forcontrolling pests, which comprises applying a composition according toclaim 7 to the pests or their environment with the exception of a methodfor treatment of the human or animal body by surgery or therapy anddiagnostic methods practiced on the human or animal body.
 10. A methodfor the protection of plant propagation material from the attack bypests, which comprises treating the propagation material or the site,where the propagation material is planted, with a composition accordingto claim
 7. 11. A coated plant propagation material, wherein the coatingof the plant propagation material comprises a compound as defined inclaim 1.